A Type 8 manager gets feedback that they’re “too intense” with their team. They don’t understand it. They’re being direct and efficient—that’s how they show respect. What they don’t see: their Type 9 employee experiences that same directness as aggression. The Type 9 goes quiet in meetings, which the Type 8 reads as agreement. The Type 9 feels steamrolled. Both people think the other is the problem.
Understanding someone’s Enneagram type is different from adapting to it in the moment—10 minutes before the 1:1, in the Slack thread that’s getting tense, when you’re writing feedback at 4pm on a Friday.
The Enneagram promises something most workplace assessments don’t: access to why people do what they do.
Motivation—what someone is trying to protect or achieve, often without realizing it.
Two managers can push equally hard for results. One because they desire to feel valuable and successful (Type 3). The other because they want to feel responsible and correct (Type 1).
Same behavior. Different drivers. And the difference changes everything about how you coach them, give them feedback, and help them grow.
That depth is why talent development leaders keep choosing the Enneagram. It reveals motivation behind behavior. It builds self-awareness deeper than most tools can reach. It explains why teams misinterpret each other. It shows each type a specific growth path. It makes emotional intelligence practical—not abstract, but something people can actually see in themselves and in others.
Those are five specific things the Enneagram is best positioned to do. And each aspect can reach further and grow stronger if it can show up in real interactions, for every employee, every day.
Get the 2026 AI coaching playbook for talent development to accelerate team performance.
How AI coaching keeps Enneagram insight accessible when managers need it most
The Enneagram can help managers understand what drives behavior amongst their team—why the Type 8 needs autonomy, why the Type 6 asks so many questions, why the Type 9 goes quiet when there’s conflict.
An AI coach equipped with a team’s Enneagram results delivers that understanding ten minutes before the 1:1 starts, before the manager writes the feedback, before the Slack thread escalates. So that all of the valuable insight does not sit dormant in a report from the workshop three weeks ago. Instead it surfaces exactly when the manager needs it—right before the interaction where understanding turns potential friction into productive conversation.
Before 1:1s: Manager gets coaching on what the employee needs to hear
Manager preparing for quarterly review with Type 2 employee who missed targets for the first time. Employee has already sent three apologetic emails.
Ten minutes before the meeting, Slack notification appears: “You’re meeting with Jordan in 10 minutes. Jordan is Type 2—driven by need for connection and appreciation. If feedback doesn’t start with how much you value their contributions, they’ll hear rejection, not guidance. Try: ‘I value your work on this team, and I want to understand what’s creating these challenges so I can support you.'”
Manager adjusts their approach. Feedback lands without triggering the “I’m failing everyone” shame spiral Type 2s fall into. Conversation stays productive.
Without AI coaching: Manager remembers Jordan is Type 2 after the meeting—when Jordan seems crushed and withdraws for the rest of the week.
During conflict: Manager sees the mismatch before tension escalates
Cross-functional project. Type 8 product manager needs decision today. Type 6 engineering lead keeps asking questions, stress-testing the plan. Type 8 reads this as stalling. Type 6 reads the push for speed as recklessness. Slack thread getting tense.
Manager preparing to step in gets coaching: “These two process authority differently. Type 8 needs autonomy and decisive action. Type 6 needs to trust the plan before committing—questions are how they build that trust, not resistance. In your conversation, validate both: ‘We need decisiveness AND a solid plan. How do we build confidence fast enough to move today?'”
Manager reframes the conflict as complementary tension, not personality clash. Both feel heard. Decision moves forward.
Without AI coaching: Manager assumes Type 6 is being difficult, sides with Type 8’s urgency. Type 6 disengages from future collaboration.
When staffing projects: Dashboard shows team composition patterns before friction starts
Manager planning project team opens dashboard showing triad distribution: 60% Gut types (8, 9, 1), 30% Heart types (2, 3, 4), 10% Head types (5, 6, 7).
The AI coaching flags a possible outcome: “Under pressure, most of this team will react with instinct and intensity. Build in space to acknowledge what’s wrong before pivoting to solutions. If you skip acknowledgment, Gut types will escalate until they feel heard, and Heart types will feel like their concerns are being dismissed.”
Manager structures communication to prevent predictable friction. Team navigates pressure without fracturing.
Now, imagine without the timeliness and proactive nature of the AI coach: Manager staffs the team. Pressure hits. Gut types spiral, Heart types withdraw. Manager doesn’t understand why collaboration collapsed.
For more on how AI coaching activates assessment insights in manager workflows, see AI for leadership development.
See How Cloverleaf’s AI Coach Works
How AI coaching prevents the Enneagram from degrading into labels among team members
Shortly after after the workshop or program, the depth of the Enneagram starts to collapse into stereotypes among the team:
- “She’s just a Type 8” (dismissive)
- “He’s such a Type 6” (frustrated)
- “Typical Type 3” (eye roll)
The team stops asking why someone behaves a certain way and starts using their Type as a shorthand explanation — or a dismissal.
An AI coach equipped with Enneagram data can help teams prevent this reduction by keeping the WHY behind each Type’s behavior pattern present whenever teammates are interacting with one another.
Consider a manager frustrated with Type 6 teammate asking endless questions in project meetings. Their internal monologue might sound like: “So negative. Always seeing problems. Can’t he just trust the plan?”
Before next project kickoff, the AI coach provides the manager with a tip: “This person is Type 6—they build confidence by stress-testing the plan. Questions aren’t resistance. They’re how this person moves from caution to commitment. Create space for questions. Show how you’ve addressed risks. That’s how they get on board.”
The manager’s interpretation can more readily shift from “He’s blocking progress” to “He needs to see risks addressed before he can commit.” Frustration becomes understanding. Questions get space instead of dismissal. Type 6 moves from caution to advocacy.
If this consistently happens, curiosity replaces judgment. The depth and value of the investment in the assessment and training drastically compounds to deliver real value to the organization through more collaboration and higher performance.
An AI coach can help managers practice self awareness using the Enneagram
Consider the workshop moment: Type 3 leader realizes they tend to skip relational connection and dive straight into deliverables. The recognition feels powerful in the moment. “I’m going to remember this and apply it.”
Next 1:1 comes around: They don’t remember. While preparing the agenda, they’re focused on project status updates and task progress. Relational connection doesn’t cross their mind because their Type 3 drive for achievement is pulling their attention to results.
An AI coach doesn’t rely on the manager’s memory or willpower to change ingrained patterns. Ten minutes before the 1:1, a notification can appear in their workflow: “Your Type 3 drive for results is a strength, but this employee may need relational connection before diving into problem-solving. Consider starting with: ‘How are you doing? What’s feeling hard right now?’ If you move straight to deliverables without this connection, you might solve the immediate task while unintentionally creating distance in the relationship.”
The Type 3 manager pauses. Adjusts their agenda. Opens the meeting with a genuine check-in instead of the status update they’d planned. The employee shares what’s actually been difficult. The conversation becomes real instead of purely transactional.
If this kind of contextual reminder surfaces consistently over time—before 1:1s, before feedback conversations, before team meetings—the repetition can help rewire the behavior pattern. The Type 3 manager may start naturally asking “How are you?” before diving into status updates—not because they consciously remembered the workshop insight each time, but because the repeated prompting helped establish a new habit.
This same dynamic can support other Types in recognizing their patterns before acting on them: Type 1 catching when their standards are tightening beyond what’s helpful. Type 6 noticing when healthy caution is tipping into analysis paralysis. Type 9 recognizing conflict avoidance early enough to address issues before resentment builds.
When this works well, self-awareness can gradually become self-management. Workshop insight becomes part of daily practice instead of remaining a powerful memory that fades over time.
AI coaching can help managers notice their stress arrows to adjust behavior before problems arise
Each Type has a predictable stress response. Type 1 standards may tighten beyond what’s helpful. Type 7 might avoid addressing present challenges. Type 6 could slide into worst-case thinking. Type 3 may over-index on achievement while losing relational connection.
Managers might not recognize their own stress pattern until after they’ve already acted on it—after the email is sent, after the meeting went poorly, after team morale took a hit.
Consider a Type 1 manager facing deadline pressure. Their internal critic amplifies. They start rewriting their team’s work. At 11pm, they send detailed feedback with 14 corrections. By morning, the team feels demoralized—the message they received wasn’t “here’s how to improve” but “nothing you do is good enough.”
An AI coach can role play with the employee. A Type 1 manager might consider sending late-night feedback — before they do, they could interact with the coach to decide how to make sure it lands how the other will best receive it.
Manager: “I need to send my team feedback on this deliverable. There are at least 14 things that need correcting.”
Coach (playing the recipient): “Reading this, I’d feel like nothing I did was good enough. The volume of corrections would overshadow any useful guidance. Can we sort through which corrections address genuine quality issues versus which ones reflect the higher bar you set when you’re under pressure?”
Manager: “I guess some of these are more about how I would have done it, not actual errors.”
Coach: “That’s your Type 1 stress pattern showing up — standards tightening beyond what’s helpful. What if you save this as a draft, revisit it tomorrow, and send only the corrections that address real impact?”
After the role play, the manager re-reads their feedback with new perspective. They recognize that roughly half the corrections came from stress-fueled perfectionism rather than actual quality concerns. They save the draft, revisit it the next morning, and send a version that addresses real issues — without the rigidity that pressure had introduced. The team receives feedback they can act on rather than a message that leaves them feeling like nothing they do is good enough.
If this kind of interaction happens consistently — before late-night emails, before tense meetings, before standards become unreachable — the manager starts recognizing their stress pattern earlier. Not after the damage is done, but while there’s still time to choose a different response.
Over time, the AI coach becomes a development partner — helping managers recognize their patterns early enough to lead with intention rather than react under pressure.
How to activate the Enneagram investment your organization has already made
If your organization completed Enneagram training, you don’t need to start over. Here’s how AI coaching activates existing insights:
Step 1: Team members enter their Enneagram types
Team members enter their type (1-9) into Cloverleaf. Takes two minutes per person.
If someone hasn’t identified their type yet, they can take Cloverleaf’s free, validated Enneagram assessment—built on the RHETI model and trusted by 970,000+ people. Takes 12 minutes. Results include core type, wings, triads, and growth/stress arrows with workplace-ready insights.
Step 2: Admins enable AI coaching
Single activation for entire organization. Managers automatically receive Enneagram-informed coaching before scheduled 1:1s in Slack, Teams, or email—based on who they’re meeting with and that person’s type.
Step 3: Managers access team dashboards
Dashboards show team Enneagram distribution across triads: Gut types (8, 9, 1) lead with instinct and action. Heart types (2, 3, 4) focus on relationships and recognition. Head types (5, 6, 7) lead with planning and possibility. Managers see where friction patterns are likely when staffing projects or navigating high-stress periods.
Step 4: Track behavior change, not workshop completion
Measure whether managers are adapting communication based on type. Track feedback quality improvements, conflict resolution effectiveness, 1:1 conversation depth.
Existing Enneagram investment becomes foundation for continuous coaching that reinforces insight at moment of need.
For organizations exploring how AI coaching creates sustained behavior change beyond training, see how to turn performance reviews into behavior change.
Common questions from talent development leaders
How is this different from managers reviewing Enneagram reports before 1:1s?
Static reports put the entire burden on the manager to remember what they read, interpret it correctly, and apply it in the moment. Most won’t — not because they don’t care, but because they’re moving between six meetings and a full inbox. The shift with AI coaching is that the relevant insight arrives at the point of need: before the conversation, inside the tool they’re already using, tailored to the specific person they’re about to meet with. The manager doesn’t have to go looking for it — it meets them where they are.
We already use multiple assessments. Does this only work with Enneagram?
No single assessment captures a complete picture of how someone communicates, what motivates them, and where their strengths sit. The more useful question is whether an AI coaching tool can synthesize across assessments rather than treating each one in isolation. When a manager is preparing for a 1:1, they shouldn’t need to cross-reference three different reports. The coaching should pull from all available data — communication style, strengths, core motivation — and deliver a unified picture that’s actionable for that specific conversation.
What does implementation look like without adding training burden to managers?
Cloverleaf scales Enneagram-informed coaching across entire organizations—whether 50 managers or 5,000. AI coaching integrates with Slack, Microsoft Teams, Google Workspace, and Workday, so coaching appears where managers already work. Each manager receives personalized guidance based on who they’re working with and that person’s Enneagram type—no individual manager setup or training required.
Most Enneagram investments peak after assessment or training is completed. The insight is real — managers see their patterns, understand their teams differently, and leave with genuine intention to change. But intention without infrastructure fades. Within weeks, Type descriptions become shorthand labels, stress patterns go unnoticed until after the damage is done, and the depth that made the Enneagram valuable in the first place collapses into stereotypes.
AI coaching changes what happens after the results are received or the training wraps up. It keeps the why behind each Type’s behavior present in the moments where understanding actually matters — before the 1:1, during the tense Slack thread, while writing Friday afternoon feedback. Not as a report the manager has to remember to consult, but as context that arrives when it’s needed and disappears when it’s not.
When that happens consistently, the shifts compound. The Type 3 manager starts checking in relationally before diving into deliverables. The Type 1 catches when pressure is tightening their standards beyond what’s helpful. The Type 6’s questions get treated as commitment-building rather than resistance. The Type 9 names a concern early instead of letting it build into quiet resentment.
That’s the difference between an assessment that holds value and a development investment that’s still working six months later. The Enneagram provides the insight. AI coaching makes it operational.
Research shows only 24% of senior executives believe their leadership development programs actually work (Corporate Executive Board). Your DISC workshop got great satisfaction scores. Managers left understanding the four behavioral styles. They know their team members are High D, High S, High I, or High C.
Three weeks later, your High D manager is still giving direct, results-focused feedback to their High S employee who needs processing time and softer delivery. The DISC awareness is there. The application isn’t.
The problem isn’t that managers forgot DISC. It’s that they’re not using it when it actually matters—before giving feedback, during conflict, when preparing for difficult conversations.
Get the 2026 AI coaching playbook for talent development to accelerate team performance.
Why managers can remember DISC profiles but still struggle to change how they communicate
The DISC assessment creates awareness to help managers understand the four behavioral dimensions:
Dominance (direct, results-oriented),
Influence (persuasive, social),
Steadiness (patient, collaborative),
Conscientiousness (analytical, detail-focused).
They can almost immediately start mapping their team. They understand this individual is High S. They know this other person is High D.
Yet, when they return to work and continue giving feedback and intereacting with each other the same way they always have.
This isn’t because the training or insights are not relevant or true. It’s a reinforcement problem.
Managers can remember the four profiles. What they don’t have is a system that surfaces DISC insights at the moment they actually need them—before giving feedback, during conflict, when preparing for difficult conversations.
Unfortunately, managers and tesms reduce the impact of DISC to explaining behavior after the fact (“Of course she didn’t respond well to my feedback—she’s High S”) instead of using it to adapt their approach before conversations happen.
Mark Flanigan, a former Analyst Manager accurately describes the gap: “I had just come back from a management training where we learned all about DISC. First thing I asked my manager was what about my employees, are they going to get DISC training? The answer was no, we don’t have the budget for that.”
His organization invested in DISC awareness for managers, but had not yet invested in a system that helps scale DISC insights so entire teams of people can actually apply its insights.
See How Cloverleaf’s AI Coach Works
The critical gap between knowing someone’s DISC style and applying the insight
When managers know their employee’s DISC style but don’t have support applying it, they face a choice every time they give feedback or prepare for a difficult conversation:
Option 1: Stop what they’re doing, look up DISC guidance for that behavioral style, remember how to adapt their approach, then return to writing feedback.
Option 2: Give feedback the same way they always do.
Most choose option 2. Not because they don’t care. Because in the moment—writing performance feedback at 4pm on a Friday, preparing for tomorrow’s difficult conversation, responding to a tense Slack thread—remembering to look up and apply DISC guidance adds friction they don’t have bandwidth for.
AI coaching solves this by putting DISC insights in front of managers when they’re actually most valuable.
For example, imagine the following scenarios that happen on a daily basis for your leaders:
Manager writing feedback to High S employee gets a Slack notification: ‘This employee needs softer delivery and time to process. Try adding specific examples and framing feedback as conversation, not critique.’
Manager preparing for 1:1 with High D employee sees: ‘This person values directness and efficiency. Get to the point quickly, focus on results.’ The manager doesn’t remember to look this up. It appears automatically when they need it.
What DISC insight can actually show up in manager workflows
Here’s what happens when DISC insights surface at the moment managers need them:
Before giving feedback: Manager gets coaching while writing the review
Manager writing performance feedback to High S employee (patient, collaborative, prefers stability) types: “Your project deliverables have been consistently late. This needs to improve immediately.”
Before the manager hits send, Slack notification appears: “This employee has High S behavioral style—they need time to process feedback and prefer softer delivery. Try: ‘I’ve noticed some delays in project timelines. Can we talk through what’s creating those delays and how I can support you in meeting deadlines?'”
Manager revises. Feedback gets delivered in a way the High S employee can actually receive.
The manager didn’t remember to “use DISC.” AI coaching prevented the communication mismatch in real-time using DISC data the organization already has.
During team conflict: Manager gets context before addressing friction
Two team members clash repeatedly. High D team member (direct, fast-paced, results-driven) sees High S team member (methodical, needs processing time) as indecisive. High S sees High D as aggressive and pushy.
Manager preparing to address the conflict gets coaching before the meeting: “This friction is pace mismatch, not personality clash. High D style prioritizes speed and directness. High S style needs time to consider options and build consensus. Help them see how these complementary styles create better decisions when both are respected.”
Manager enters the conversation prepared to reframe the conflict as style difference instead of letting “He’s just a High D” become the explanation.
When staffing projects: Dashboard shows team DISC gaps before friction happens
Manager planning project team opens dashboard showing DISC distribution: 65% High I/High D (fast-paced, social, results-oriented), 20% High C (detail-focused, analytical), 15% High S (steady, collaborative).
Coaching flags the gap: “This team will generate ideas and momentum quickly but may skip planning and miss details. High C team members will feel rushed. Build in time for detailed planning before execution. Assign High C team member to review work for accuracy before deadlines.”
Manager staffs the project knowing where friction will occur and how to prevent it. Not because they remembered to analyze DISC distribution manually—because the dashboard surfaced the insight when they needed it.
For more on how AI coaching supports managers in specific workflows, see AI for leadership development.
How to activate your DISC data with AI Coaching
Your organization may have already completed DISC assessments. If so, you don’t need to re-assess. Here’s how to activate that data with AI coaching:
Step 1: Team members enter their existing DISC styles
If your team already completed DISC assessments through another provider, team members can enter their behavioral styles (Dominance, Influence, Steadiness, Conscientiousness) into Cloverleaf. Takes two minutes per person.
If team members haven’t taken DISC yet, they can take Cloverleaf’s free, validated DISC assessment in 10 minutes. Built on Marston’s theory and verified with 48,000+ users, it provides instant results showing their blend of all four styles—not just a single category.
Step 2: Admins enable AI coaching
Single activation for entire organization. Managers automatically receive DISC-informed guidance before scheduled 1:1s in Slack, Teams, or email—based on who they’re meeting with and that person’s DISC style.
Step 3: Managers access team dashboards
Dashboards show team DISC distribution. Managers see whether their team is heavy on High D/I (direct, fast-paced, results-oriented) or High S/C (steady, analytical, process-focused) when staffing projects and diagnosing team friction.
Step 4: Track behavior change, not completion rates
Measure whether managers are adapting communication. Track feedback quality improvements, conflict resolution effectiveness, team collaboration scores—not just “managers completed DISC training.”
Your existing DISC investment, or Cloverleaf’s free DISC assessment, becomes the foundation for continuous AI coaching that can also support future trainings and workshops.
FAQ’s about DISC assessment and AI coaching
Don’t managers just need to remember to use DISC?
In theory, yes. In practice, managers preparing for difficult conversations, writing feedback under deadline, or responding to team conflict don’t have bandwidth to stop, look up DISC guidance, and apply it. AI coaching removes that friction by surfacing guidance automatically when managers need it—not when they remember to seek it out.
How is this different from sharing DISC reports on a shared drive?
Three differences: Automatic notifications before 1:1s (managers see DISC insights without remembering to look them up). Team dashboards show DISC distribution patterns managers can’t calculate from individual reports. AI coaching provides situation-specific guidance on how to adapt communication, not just raw DISC data.
Can DISC with AI coaching scale in large enterprises?
Cloverleaf scales DISC-informed coaching across entire organizations—whether you have 50 managers or 5,000. AI coaching integrates with Slack, Microsoft Teams, Google Workspace, and Workday, so DISC-informed guidance appears where your managers already work. Each manager receives personalized coaching before their 1:1s based on who they’re meeting with and that person’s DISC style—without adding administrative overhead or requiring individual manager setup.
We use other assessments too. Does this only work with DISC?
Cloverleaf integrates multiple assessments (DISC, CliftonStrengths®, Enneagram, 16-Types, Insights Discovery). When managers have multiple assessment data points, AI coaching pulls from all sources to provide richer behavioral context. For more on how CliftonStrengths® activates with AI coaching, see CliftonStrengths® with AI coaching.
DISC assessments and training can create awareness. Roughly 76% of organizations with more than 100 employees use behavioral assessments. Most of that DISC data sits unused after the initial workshop because managers don’t have a system that surfaces insights when they actually need them.
AI coaching can proactively deliver DISC insights in front of managers before they write feedback, before they address conflict, before they staff projects. A workshop or coach can help teach managers what DISC is. AI coaching can continuously show them when and how to use it in their unique situations and interactions with team members. Assessment data that has sat in reports long after the assessment occurred can become personalized, proactive coaching that appears automatically before every conversation that matters to a team’s performance.
Research shows only 16% of employees have meaningful conversations with managers weekly (Gallup). Your organization invested in CliftonStrengths® to fuel those conversations, team members know their Top 5, attended debrief workshops, understand their strengths.
Just a few weeks later, your managers can’t remember if their direct report has Achiever or Activator when preparing for 1:1s. The meaningful conversations CliftonStrengths® can unlock over the long haul? Not happening.
The assessment data exists. Your people know their strengths. The problem is your managers can’t remember everyone’s CliftonStrengths when they actually need them. The data sits in a PDF somewhere. Your manager needs it in Slack before the 1:1 that starts in 10 minutes.
Get the 2026 AI coaching playbook for talent development to accelerate team performance.
How AI coaching uses CliftonStrengths data in manager workflows
AI coaching puts CliftonStrengths® data in front of your managers when conversations happen—with specific guidance on how to use it.
Before 1:1s, managers see CliftonStrengths® with coaching on what to ask
Ten minutes before a manager’s 1:1 with Sarah, they get a Slack notification: “You’re meeting with Sarah in 10 minutes. Her CliftonStrengths® Top 5: Achiever, Arranger, Responsibility, Discipline, Focus (all Executing domain).”
AI coaching adds: “Sarah has Achiever—she gets energy from progress made, not just goals remaining. Ask: ‘What milestones did you hit this week that you’re proud of?’ Avoid spending the meeting on aspirational planning—she wants to talk about what she’s accomplished.”
Your manager enters the conversation knowing how Sarah works and what questions will resonate.
When staffing projects, managers see team domain balance they’d never calculate manually
Manager planning a project team opens the dashboard: 60% Strategic Thinking, 15% Executing, 20% Relationship Building, 5% Influencing.
AI coaching flags the gap: “This team generates great ideas but struggles to ship. Staff someone with Executing domain strengths—Achiever, Arranger, Discipline—or add process checkpoints to drive completion.”
The project doesn’t stall three months in because everyone’s good at strategy but no one closes.
During conflict, managers understand personality friction instead of personality clash
Two teammates keep clashing. Manager checks CliftonStrengths® comparison: Person A has Activator (wants to start immediately, momentum-driven). Person B has Deliberative (needs time to consider, risk-aware).
AI coaching: “This isn’t personality conflict—it’s complementary strengths creating friction. Help them see how Activator energy plus Deliberative caution creates better decisions than either alone.”
After projects derail, managers diagnose why using inactive strengths
Project missed deadline. Manager checks dashboard: Zero Executing domain strengths. Lots of Strategic Thinking and Influencing. Great vision, momentum, but no one wired to drive completion.
One manager described this: “I’ll look at inactive strengths and go, ‘Oh, that’s why that went wrong. We didn’t have any Adaptability. Next time we staff differently or add process.'”
This pattern recognition your managers can’t do when strengths data sits in individual PDFs.
See How Cloverleaf’s AI Coach Works
How managers can use CliftonStrengths® data to improve coaching, assignment outcomes, and performance conversations
Here are just a few ways AI coaching can support specific manager workflows:
Pre-coaching call with sales rep
Before supervisor’s coaching call with rep, AI coaching surfaces: “[Rep’s name] has Achiever + Competition. Frame conversation around wins this week and where they rank against quota. Skip lengthy strategic planning—they want action, not analysis.”
Supervisor knows how to structure the conversation before it starts.
Territory assignment decisions
Dashboard shows sales team domain distribution: Heavy on Influencing/Relationship Building, light on Strategic Thinking. AI coaching: “Assign high-touch, relationship-driven territories. For complex deal strategy, pair with someone who has Strategic Thinking strengths.”
Staffing decisions match how people naturally work.
Performance improvement conversations
Rep struggling with quota. CliftonStrengths® shows Learner + Input (Strategic Thinking domain). AI coaching: “Not a motivation problem—they’re drowning in information, not converting to action. Pair with mentor who has Executing strengths to model closure behaviors.”
The intervention addresses actual root cause instead of generic “try harder” feedback.
First-time manager transitions
Sales IC promoted to first-time manager. Before their first team meeting, AI coaching: “Your team has 3 Competitors, 2 Achievers, 1 Harmonizer. Expect push for individual recognition. Balance competitive energy with team cohesion rituals.”
New manager enters role with team intelligence, not just management theory. For more on supporting new managers through transitions, see how to support new managers in their first 90 days.
How to activate CliftonStrengths® data your team already has
If your organization already completed CliftonStrengths® assessments, you don’t need to re-assess. Here’s how to activate that data with AI coaching:
Step 1: Schedule a consultation with Cloverleaf
Talk with a Cloverleaf expert about your team size, development goals, and whether you need team AI coaching or assessment consolidation.
Step 2: Team members add their existing Top 5
No need to retake the assessment. Team members enter their CliftonStrengths® Top 5 from previous Gallup assessments into Cloverleaf. Takes two minutes per person. (If someone hasn’t taken CliftonStrengths® yet, some Cloverleaf plans include Gallup access codes.)
Step 3: Enable AI coaching for your teams
Admins turn on coaching notifications. Managers automatically receive CliftonStrengths®-informed coaching before scheduled 1:1s—in Slack, Teams, or email.
Step 4: Give managers access to team dashboards
Managers see their team’s domain distribution (Strategic Thinking, Executing, Influencing, Relationship Building) when staffing projects and running retrospectives.
Step 5: Track meaningful conversation frequency
Measure whether managers are having more strengths-informed conversations, track monthly as coaching becomes active.
No re-assessment required. No additional workshop facilitation. Your existing CliftonStrengths® investment becomes the foundation for continuous AI coaching.
For organizations exploring how AI coaching extends leadership development beyond workshops, see AI for leadership development.
How AI coaching interprets CliftonStrengths® for specific manager conversations
AI coaching doesn’t just show raw CliftonStrengths data. It interprets what that data means for the specific situation about to happen.
AI coaching recognizes theme combinations
Manager has Learner + Input + Achiever.
Static report says: “You like learning. You collect information. You’re driven.”
AI coaching can understand and nuance to provide specific, personalized suggestions and guidance: “Your Learner + Input combination means you naturally collect information. Your Achiever means you want to DO something with what you’ve learned—not just accumulate knowledge. Try creating a resource library for your team or documenting processes as you learn them. This uses all three themes.”
AI coaching can proactive support the conversations about to happen
Static report: “Sarah has Achiever.”
AI coaching before 1:1: “Sarah has Achiever—she gets energy from progress made. Ask: ‘What milestones hit this week?’ not ‘What’s left on your list?’ Frame feedback around accomplishments, not just remaining work.”
Different coaching for different situations using the same CliftonStrengths® data.
Common questions from talent leaders
Do we need to re-assess our entire team?
No. Team members enter their existing CliftonStrengths® Top 5 from previous assessments. Takes two minutes per person. If someone hasn’t taken CliftonStrengths® yet, they can take it through Gallup and enter results. Some Cloverleaf plans include Gallup access codes—check with your HR team or schedule a consultation to learn more.
How does this work at scale for 500+ managers?
Cloverleaf scales personalized CliftonStrengths® coaching across your entire organization—whether you have 50 managers or 5,000. AI coaching integrates with Slack, Microsoft Teams, Google Workspace, and Workday, so CliftonStrengths-informed guidance appears in the flow where your managers already work.
How is this different from sharing CliftonStrengths® reports on a shared drive?
There are a few differences: Proactive coaching before 1:1s (managers don’t have to remember to look up PDFs). Team dashboard shows domain balance patterns managers can’t calculate from individual reports. And, AI coaching provides personalized, situation-specific guidance on what to say and ask, not just raw data.
Only 16% of employees have meaningful conversations with managers weekly. CliftonStrengths workshops create valuable insights—your people understand their Top 5, managers see how teams are wired.
AI coaching puts those insights in front of managers when conversations happen. Before 1:1s in workplace tools. In dashboards when staffing projects. With specific guidance on what to say based on who they’re talking to.
Valuable insights shared in important trainings show up in daily work. In the moment discovery becomes continuous application. Assessment data that sits in PDFs becomes coaching for every employee conversation.
Click here for more on using CliftonStrengths® with Cloverleaf’s AI Coach.
Customer support onboarding at Wix used to take three months. Agents had to memorize complex product knowledge across multiple offerings—websites, e-commerce, bookings, blogs. By month three, they’d forgotten what they learned in month one. And the product changed so fast that memorized knowledge became outdated anyway.
Dr. Eli Bendet-Taicher, Head of Global Learning & Talent Development at Wix, and his team built an AI-supported knowledge discovery agent. Agents can now find relevant internal resources in seconds, get simplified explanations of complex procedures, and receive suggested responses that adapt to customer context.
Onboarding dropped from three months to one month. Training that remained focused on judgment, communication, and customer empathy—the human skills AI can’t replace. Technical knowledge became instantly accessible instead of memorized.
But not every AI implementation at Wix succeeded. Eli’s team also built personalized learning paths that employees didn’t use. Sarika Lamont, Chief People Officer at Vidyard, discovered AI tools that promised productivity created multitasking overload instead. Christina Parr, Global Talent & Organizational Design Leader, watched team members lose credibility by dumping uncustomized AI outputs into Slack.
What actually works when implementing AI in talent development—and what fails in ways that waste time, budget, and credibility? Three practitioners recently shared their real implementation stories: the wins, the disappointments, and what they’d do differently.
Get the 2026 AI coaching playbook for talent development to accelerate team performance.
Why personalized learning paths failed (and what employees actually needed)
Eli’s team built personalized learning paths on their LMS. The AI would analyze each employee’s role and history, then suggest what they should learn next. On paper, it sounded perfect.
Employees didn’t use it.
“People weren’t struggling with what to learn,” Eli said. “They were struggling with clarity, with time, with priority, with support and coaching.”
The AI solved a problem that didn’t exist. Employees don’t become suddenly engaged because a system suggests smarter course sequences. They become more effective when AI helps them solve problems faster in their actual workflow.
AI can’t redesign motivation. AI removes friction.
When AI creates more problems than it solves
Sarika Lamont, Chief People Officer at Vidyard, identified another failure pattern: AI tools that promise productivity but create multitasking overload.
“There’s a great HBR article that just came out on how AI doesn’t reduce work—it intensifies it,” Sarika said. “We’re multitasking even more. We’re code-switching and context-switching even more. I’ve got six different tasks going on in multiple different tools and my brain is fried.”
The excitement about what AI can do leads people to try everything at once. One of Vidyard’s software engineers joked that he’s working on becoming better at ADHD because he’s so good at focusing—he needs to improve his ability to switch between tasks constantly.
People need to slow down to speed up. But organizations don’t know how to create that space.
See How Cloverleaf’s AI Coach Works
The credibility problem with generative AI
Christina Parr, Global Talent & Organizational Design Leader, shared what happens when teams rely on generative AI without customization.
“We had a new team member who would see the team talking on Slack or Teams about needing a tool for something. This person would go out to AI, ask for exactly what we were asking for, and just dump the document into Slack,” Christina said. “It was not effective. It took away from that person’s credibility because it wasn’t at all customized to what the team actually needed.”
Generative AI can draft quickly. Human judgment determines whether the output is actually useful.
For more on how talent development infrastructure changes when AI handles friction, see why 2026 is the year talent development becomes business infrastructure.
What to measure instead of logins: Time saved, promotions, and manager effectiveness
Login metrics don’t prove AI delivers value. When development happens in the flow of work instead of behind a login wall, you need different measurements.
Eli outlined three categories for measuring AI impact:
Operational efficiency: The straightforward calculation
Time saved creating materials. Faster access to knowledge. Shorter onboarding cycles.
“For us, reducing onboarding from three months to one month—that’s ROI right there,” Eli said. “Two months of training cut off. You know how much money that costs.”
Calculate reduced hours multiplied by cost per hour. This is the easiest layer to measure and defend.
Performance outcomes: Business KPIs that improve
Time to productivity. Error rates. Customer satisfaction. Manager effectiveness.
When AI embeds in workflows, business KPIs attached to the behaviors you’re trying to change should improve. Wix tracks customer support metrics—response time, resolution time, customer satisfaction scores. Those metrics improved when agents could find answers instantly instead of escalating or guessing.
Vidyard explores rep productivity and quota achievement. Can individual reps handle higher quotas when AI improves their workflow? That’s a performance outcome with direct revenue impact.
Decision quality: The hardest to measure, most important to track
Can managers give better feedback faster? Can they identify skill gaps earlier? Do internal mobility and promotion rates improve?
“This is the trickiest pillar but actually one of the most important ones that’s being overlooked,” Eli said. “AI tools that help us make better business decisions on the fly—that’s what we should be measuring.”
Organizations using AI coaching see measurable differences here. Employees who engage with AI coaching get promoted at 3x the rate of those who don’t. Managers give feedback more frequently and more effectively when they receive prompts before one-on-ones.
Internal mobility increases. Retention improves. Team performance strengthens over time.
Function-specific metrics matter more than organization-wide KPIs
Sarika emphasized that KPIs need to be function-specific, not one-size-fits-all.
“What ROI looks like for sales is going to be different for engineering,” she said. “I’m putting the onus back on those leaders—you tell me what problem you’re trying to solve, and then we tie measurable outcomes specifically to that.”
Sales might measure rep productivity and quota achievement. Engineering might measure developer experience survey scores and engineering output. HR might measure time to fill positions and quality of hire.
The mistake is trying to create one organization-wide AI success metric. The win is helping each function measure AI’s impact on their specific business outcomes.
For more on how AI coaching enables measurement beyond activity metrics, see how AI coaching works.
How to navigate security requirements without getting stuck
Security concerns stop more AI implementations than any technical limitation.
“Our security team is nervous about me putting personally identifiable data in AI tools like Claude and OpenAI,” one talent leader asked during the webinar. “It’s really limiting our ability to move forward. What are tactical tips?”
Start with your CIO as your partner, not your barrier
“Your CIO should be your bestie,” Christina said. “Start with a committee that includes your CTO, CIO, chief information security officer, your risk person, the head of HR. You may even want someone who heads procurement.”
This isn’t about getting permission. This is about building a policy together that addresses real risks while enabling real work.
Develop a people-specific AI policy, not just a generic AI policy
Generic AI policies cover broad usage. People-specific AI policies address:
- What tools are approved for HR data
- Where human judgment is required versus where AI can decide
- How personally identifiable information gets handled
- Who has admin rights and what those rights mean
- Tool-by-tool risk assessment and access levels
“We started to get a lot more specific to each tool,” Sarika said. “Who has access to what, who has admin rights, and what does it mean to have admin rights. Because there’s AI incorporated in our new performance tool, employees are much more sensitive about what this data is being used for, who has access to it, how we’re using it. These were never questions we were asked with our pre-AI performance tool.”
Anticipate vetting processes and plan accordingly
Wix’s vetting process for AI vendors is “gruesome,” according to Eli. “It can take a long long long amount of time. But we do approve certain vendors that use AI.”
The process can involve figuring out security requirements that didn’t exist before. Things change so fast that what one organization figures out may not be repeatable three months later.
Security requirements will slow you down. Partnership with IT and procurement speeds you back up.
Ask vendors for SOC 2, ISO certifications, and clear data handling documentation
Don’t guess what security documentation you need. Ask vendors directly:
- SOC 2 Type II certification
- ISO 27001 certification
- GDPR alignment documentation
- Data encryption standards
- Where data is stored and who has access
- Whether customer data trains AI models (it shouldn’t)
Vendors building for enterprise understand these requirements. If a vendor can’t provide documentation quickly, that’s a red flag.
4 steps to start implementing AI in talent development
The practitioners offered specific next steps for organizations in planning or pilot phases.
1. Run pilots and expect messiness
“We are going through these procurement processes all the time. No two are exactly the same,” Kirsten Moorefield noted. “Things change so fast right now. The goals—what AI offers—are so good, but everyone is really trying hard to figure it out. Optimistic persistence, everybody.”
Pilots reveal what works in your specific context with your specific people. Generic best practices don’t translate directly. Your culture, your workflows, your security requirements create unique implementation challenges.
2. Focus on workflow redesign, not just tool adoption
Adoption is the first step. Real outcomes require rethinking how work gets done.
Sarika shared Zapier’s approach: they created automation engineer roles. These aren’t people who also deliver against functional OKRs. Their full-time job is redesigning workflows using AI within their function.
“In talent acquisition or the people function, they’ve got someone who’s an HR automation engineer,” Sarika explained. “She’s been in HR so she understands the processes. No one has to teach her that. But she also understands the products really well. She can take a problem and figure out how it could be redesigned using different tools and orchestration.”
Most organizations can’t afford dedicated roles yet. The principle holds: someone needs dedicated time to redesign workflows, not just train people on how to use AI tools.
3. Ask vendors to help you measure impact beyond activity metrics
Vendors can track metrics traditional HR systems couldn’t see.
“Work with your vendors on how to get these metrics,” Kirsten said. “We’ve done this customized with different customers. You really can be very creative and ask for anything. The worst that can happen is somebody says no.”
Organizations using Cloverleaf’s AI coach see employees get promoted at 3x the rate of those who don’t engage with coaching. That metric exists because customers asked for it.
What metrics matter for your organization? Ask vendors if they can track it. If they can’t now, they might build it if enough customers request it.
4. Decide build versus buy based on speed and complexity
Sarika wrestled with whether to build custom AI tools or buy existing platforms.
“The question still remains: Do I really need to be thinking about building? Because I don’t actually think the build always works. Sometimes buying makes more sense because that particular platform has maybe figured out something that connects more of the dots that I can’t connect—and it’s faster.”
Building makes sense when you’re orchestrating multiple tools with organization-specific data. Buying makes sense when a platform solves a complete problem and integrates with your existing systems.
The answer isn’t always one or the other. Sometimes you buy multiple tools and build the orchestration layer in the middle.
For guidance on supporting managers through transitions with AI coaching, see how to support new managers in their first 90 days.
The three biggest AI implementation failures share a common root: solving the wrong problem, expecting too much too fast, or skipping the human judgment step. The wins share a pattern too: removing friction from real workflows, measuring business outcomes instead of activity, and giving people dedicated time to redesign how work happens.
Security requirements and procurement processes will slow you down. Partnership with IT and vendors who understand enterprise needs speeds you back up. Start with pilots. Expect messiness. Ask vendors for custom metrics. And remember: AI adoption is the beginning, not the goal. Real transformation happens when workflows change.
Performance reviews, succession planning, and engagement surveys surface critical development insights. But their impact depends on employee follow-through.
The challenge isn’t generating talent data—most organizations have plenty of that sitting in Workday. The challenge is activating that data so it actually changes behavior. When development insights live in systems employees have to remember to check, they get buried by daily work demands.
AI coaching surfaces Workday data as guidance in the tools employees use daily—a Slack message before a difficult conversation, coaching in Teams before a one-on-one, or prompts in email when giving feedback.
Get the 2026 AI coaching playbook for talent development to accelerate team performance.
What’s different about AI coaching inside Workday
There’s a wealth of information that lives in Workday and other core HR systems. Performance reviews. Engagement data. Feedback. Succession plans. The question is: how do we tap into that to really customize and personalize coaching for individuals?
Historically, coaching was really only accessible to the top one to three percent of people in an organization, and it was very expensive at that. For the same amount of money that you were spending to reach that top one percent, with an AI coaching solution, you could really get that out to the entire organization.
But here’s what makes integration different from just “making coaching available”: it’s about layering behavioral coaching on top of existing Workday functionality rather than asking people to go somewhere else.
Coaching at the point of action
Take feedback inside Workday. When you go to give feedback on someone, AI coaching can immediately pull in your feedback style—how you’re naturally wired to give feedback and how the other person likes to receive it.
Then you type in what you’re trying to communicate, and the coaching responds: “Here’s how you’re likely approaching this. Here’s how this person wants to receive it. You did a good job of this, but maybe make sure you start with an affirmation.” And then: “Can we go a step further? Here’s some additional things you might want to consider adding.”
That capability only exists at the point in time when you’re giving feedback. Whether it’s lightweight for a weekly one-on-one or something you’re writing up for the end of year, there’s a richness you can layer on top of how people are already engaging with Workday that just takes it to the next level.
This isn’t about replacing training programs or learning content. It’s about the sustainment strategy. Training can teach things like feedback frameworks. AI coaching surfaces those same frameworks right before managers need them—when they’re about to give feedback, not weeks after the workshop.
See How Cloverleaf’s AI Coach Works
How HRIS integration activates coaching when it matters
One of the beautiful things about building on top of Workday is the ability to tap into organizational context and build on top of features and capabilities that already exist. HRIS integration means coaching knows who reports to whom, when promotions happen, when performance reviews are completed, and when teams restructure—and responds to those changes automatically.
Coaching responds to what’s changing in someone’s role
Many tools integrate with Workday primarily to keep employee records and org charts current. Coaching may be available, but it isn’t connected to what’s actually changing in someone’s role, team, or responsibilities.
When someone gets promoted in Workday, the system detects this during daily sync and delivers leadership transition coaching within 24 hours—before their first meeting as a manager.
Here’s a real example:
We had three people undergoing a pretty massive change in their roles. Maybe half of what they were doing no longer was a key part of their responsibilities.
That uncertainty and fear was real—it was impacting not only their experience at work but also affecting their ability to actually do the work they were doing today, let alone navigate the change meaningfully.
I was able to go into the system and say, “I want to coach this leader through this change in a way that respects the needs and challenges that these three people are feeling.”
The system understood that those three people reported to this particular leader, and then it gave a very specific three-week strategy—reminders, role-play opportunities, very specific approaches to each person.
One of them needed repetition and information delivered in a certain way. Another needed it to be more collaborative. The system gave different strategies that allowed the leader to navigate this change in a way that avoided unnecessary struggle.
The behavioral context layer
What makes this different from generic AI coaching is the behavioral context. Cloverleaf uses assessment data—whether it’s Enneagram, DISC, or other tools—and break those individual traits and characteristics down to literally thousands of data points.
Cloverleaf connects those data points to very specific challenges people are facing in their day-to-day work life. By having access to all of that information and looking at the individual context, the people involved, the power dynamics, and the past feedback and experiences they’ve had with each other, there’s just a richness and depth that goes far beyond just knowing someone’s assessment type.
For more on how behavioral infrastructure operationalizes development frameworks, see how talent development frameworks need behavioral infrastructure.
How this solves the forgetting curve problem
The biggest challenge with traditional learning and development models is the forgetting curve. Within the first day—within twenty-four hours—you forget about seventy percent of what you learn. And by the end of a week, you’ve forgotten well more than ninety percent of what you learned in those sessions.
Sustainment strategy, not replacement
AI coaching doesn’t replace coaches, facilitators, or internal learning and development professionals. It enhances and accelerates the work they’re doing. Whether it’s coaches delivering programs or learning professionals standing up in front of a room delivering great content, there is additional context and experience that happens in those contexts that’s really important.
But having a digital solution that comes alongside those tools, where employees are working, really helps sustain that learning so the forgetting curve isn’t as steep. More importantly, they can apply it at the points in time where they need it.
We all know that learning is most effective when people have an opportunity to actually practice it. It’s not just theory—it’s specific to the people they’re leading or specific to the people they’re engaging with on a daily basis.
Meeting people in the tools they actually use
Most salespeople primarily work in email because they’re interacting externally with customers and prospects. But product and engineering teams live in Slack or Microsoft Teams every day.
Cloverleaf has built integrations so AI coaching can come to people in the tools they want to use. And we give them the ability to configure that experience so they get to choose how and when they interact.
The tool is going to give them great suggestions regardless, and then they get to pick and choose how often or how frequently or where they’re engaging with us.
There’s a fine line between being intrusive and being valuable, and putting employees at the center of the experience—letting them configure exactly how they want to interact—is what allows us to overcome data privacy challenges while ensuring coaching actually shows up when it’s useful.
What this means for talent development leaders
When you activate talent data that already exists in Workday—performance reviews, engagement surveys, succession planning, organizational changes—and connect it with behavioral context from assessments, you create coaching that’s personalized to individuals, contextual to the moment, and delivered where work actually happens.
This isn’t about adding another system for people to log into. Coaching layers onto the processes and tools they’re already using, so the insights you’ve invested in generating actually translate into behavior change.
Feedback training from a workshop surfaces as coaching before a manager’s next one-on-one. A development goal from a performance review reappears when an employee starts a project where that capability matters. Assessment insights activate when team composition changes.
To learn more about how Cloverleaf integrates with Workday to turn talent data into daily coaching, see Workday AI coaching integration. You can also explore the Cloverleaf app on Workday Marketplace.
New managers are stepping into a role they’ve never done before, expected to lead people they don’t yet understand, often without the insight or support to do it well.
What makes this particularly challenging: the people who get promoted to people leadership are the people who are really good at doing the job—doing the tasks, knowing the competencies, the skills they need to perform. But not necessarily at leading people. They don’t necessarily have a track record of being really good at advocating for people, at developing people, at coaching their peers, at giving hard feedback.
The first 90 days are when patterns get established. When a new manager either builds confidence or develops habits that will hold them back for years. So let’s find ways to support our managers in their first 90 days.
Get the 2026 AI coaching playbook for talent development to accelerate team performance.
What new managers need from day one
First-time managers immediately struggle all with the same thing. And that is being able to see all of their different individual employees and know what they need for success. Know how they get motivated. Know how they handle stress and challenge. Know how they handle change. Do they embrace it? Do they hide from it?
Every employee is going to be different. And the manager needs to be ready to lead every individual in their strengths and aware of their blind spots. But the managers are given no insight into this information and no support and training into how to actually implement support to every employee.
Yes, we may, in the best case scenarios, train them on one-size-fits-many frameworks, but that is not helpful in the flow of work when they are just too busy to go back and recheck a training that they had and when what works for one person doesn’t work for another.
Even new leaders with the best of intentions—who in interviews talked about how they want to support employees, talked about who developed them and how great it was for their career and how they want to give that back—those good intentions don’t withstand the stress of reality when the manager simply is a deer caught in headlights and does not know what to do.
See How Cloverleaf’s AI Coach Can Support New Managers
How to provide insight new managers need in the first 90 days
The first 90 days are when patterns get established. When a new manager doesn’t know how to read their team, doesn’t have insight into individual differences, and doesn’t get support in those early critical conversations, they default to what feels safe: treating everyone the same, avoiding difficult conversations, or mimicking whatever management style they experienced themselves—even if it wasn’t effective.
Give new managers the data they need to understand their team
Today, we can take all the data that we have on what matters to that manager—who are they leading? What’s their past performance review? What’s their career path and goals? What is true in the employee engagement surveys of that team?
We can combine that with real-time context: Who are they meeting with? What’s happening on their calendar? What is their own development goal?
And put those together with an AI coach that can come into their flow of work and nudge them before their one-on-ones. Nudge them with the leadership competencies that matter to your organization. Give them outlets where they can practice conversations with role play or process thoughts with an AI coach that will help them understand their own unique strengths and how to approach a situation.
New managers need both tactical information and behavioral insight
Sometimes the information they need is tactical—yes, this is what you should focus on in your first one-on-one with this employee, or this is how this person prefers to receive feedback.
But often the insight they need is more about building their inner confidence, their wisdom, their fortitude to overcome what blocks them as a leader from having successful, uncomfortable conversations.
Maybe it’s helping them not to talk most of the time and not to steamroll the conversation, but helping them ask the right questions to better understand the perspective of the employee.
Maybe it’s helping them understand that as a manager, they care a little too much about being liked and there are actually tactics they can employ to care more effectively about holding accountability—because that is truly caring for the employee. It’s helping them grow.
Behavioral assessments reveal what new managers can’t see on their own
Whatever it is, every individual has our own complicated blockers that keep us from engaging in coaching, engaging in accountability, engaging in developing the people around us. And the best informed AI coaches can know this.
That’s why organizations partner with leading behavioral assessments like DISC, Enneagrams, and Clifton StrengthsFinder. These assessments help unveil the complicated thought patterns that every individual has—patterns that hold us back or make us go a little too far too fast.
All of that can be exposed, understood, and used to inform the AI coach, along with all that HR data, to help every single person develop themselves and develop each other. And especially for new managers stepping into their first leadership role, this support can mean the difference between confidence and confusion in those critical first weeks.
Building the foundation before the transition happens
In organizations that have been equipping their managers with AI coaching for years, they have a whole culture of understanding each other, of developing each other—not depending just on leaders, but every employee being able to grow in their emotional intelligence and grow in their ability to have candid conversations with each other, upwards, downwards, or sideways, whoever they are working with.
They have developed their relationships and their capacity and their wisdom and their strength to lean into the situation with the people around them.
The compounding effect: culture before promotion + support during transition
When that’s the case, when you have that before people get promoted, plus then you have all that support for them after they’re promoted into people leadership, you have the culture that supports them as well as the tools and the information that supports those new first-time managers.
That’s the opportunity: not just fixing the first 90 days after someone’s promoted, but building the cultural foundation before promotion happens so that when someone steps into leadership, they’re not starting from zero.
What this means for your new manager support
Supporting new managers in their first 90 days means giving them what training alone can’t provide:
- Insight into the specific people they’re leading
- Guidance before the conversations that matter most
- Support that shows up in their flow of work—not in a system they have to remember to check
When you combine that cultural foundation with support in those critical first 90 days—when managers get insight into their team, guidance before difficult conversations, and coaching that helps them see individual differences from day one—you’re not just reducing new manager struggle.
You’re building managers who can actually lead people, not just manage tasks.