Last month, we talked about employee onboarding and how a great first year can shape someone’s entire experience inside a business. This month, we’re zooming in on a group whose onboarding experience often doesn’t get enough attention – managers and executives.
When you bring a new leader into the mix (or promote one), you’re not just impacting one person. You’re impacting every person they lead, collaborate with, and influence. Because of that, their first year deserves structure, clarity, and support, not guesswork. Below, you’ll find three straightforward onboarding timelines:
- New Managers
- Promoted Managers
- New Executives
Use them as roadmaps to help your leaders get grounded, build relationships, and start making an impact sooner, without burning out or stepping on landmines.
Onboarding New Managers: A Clear Year-One Timeline
Pre–Day 1: Set the Stage
Before they ever show up, help them walk in confidently by giving them context, not surprises. A little clarity ahead of time removes a lot of nerves on day one. This might include:
- A “Leadership Starter Pack” with role expectations, decision-making norms, and company acronyms
- A simple overview of the team’s current goals
- An org chart with key partners highlighted
- A welcome message from you (and ideally the team)
Week 1: Connection Over Speed
Week one isn’t about rushing into decisions, it’s about people and context. This is the week where trust starts forming. Set them up with:
- Dedicated time to meet each team member
- A walkthrough of rhythms and norms (meetings, communication expectations,
- response times, etc.)
- Introductions to cross-functional partners
- A one-on-one schedule with their direct reports
First 30 Days: Listen, Learn & Build Early Wins
Managers spend most of this phase absorbing how the business works. These early wins boost confidence, and confidence fuels momentum. Support them by:
- Sharing a Manager Toolkit (templates, one-on-one agendas, feedback guides)
- Beginning foundational leadership training (coaching, documentation,
- conversations)
- Helping them identify a small but meaningful early win
- Holding a 30-day check-in
Days 30–90: Stepping Into Ownership
This phase is where a manager begins truly leading. By the end of this window, they should feel steady and capable. Help them:
- Transition into owning meetings, communication, and workflows
- Shadow peer managers to see different leadership styles
- Complete 60- and 90-day check-ins
- Meet with your leader (skip-level) to get broader context
- Start cross-department collaboration
- Connect with a mentor or internal coach
Six Months: Steady Leadership & Stronger Impact
At this point, they’re out of the “new” phase and into true contribution. Encourage them to:
- Lead an initiative or improvement project
- Engage in deeper career conversations with their team
- Expand cross-functional work
- Participate in leadership development training
- Reflect on what’s working and where they want to grow
Use the six-month mark as a reset button to realign expectations.
One Year: Celebrate, Reset & Plan Ahead
The one-year milestone matters. Take time to acknowledge it.
- Host a forward-looking review
- Revisit their long-term career path
- Talk about compensation growth
- Celebrate the milestone meaningfully
- Set new leadership goals for Year 2
Onboarding Promoted Managers: A Smoother Shift From Peer to Leader
Promoting a high-performing employee into management is exciting, but it also comes with its own set of challenges. Navigating the “peer to manager” transition can be awkward, emotional, and confusing without support. Here’s a timeline to make it smoother.
Before the promotion becomes official, talk openly about:
- How their role will shift
- What boundaries may need to change
- How to reset relationships with former peers
- What you’ll expect from them as a leader
Also share:
- A transition communication plan
- One-on-one and team meeting templates
- A mentor or coach they can lean on
This sets them up to walk in with confidence and avoid tension.
First 30 Days: Build Credibility With Clarity
Help them focus on:
- Getting into a regular one-on-one rhythm
- Being transparent with their team about how they want to lead
- Early leadership training (especially feedback, expectations, and documentation)
- A 30-day check-in to talk about how the transition feels (emotionally and
- practically)
This is a big identity shift, so normalizing the discomfort really helps.
Days 30–90: Find the Leadership Voice
Promoted managers often need reassurance and structure during this period. This is the phase where they start trusting themselves as leaders. Give them:
- A mentor or internal coach
- 60- and 90-day check-ins
- Shadowing opportunities
- Skip-level time with your leader
First Six Months: Real Leadership Sets In
By now, they should feel more settled. Promoted managers thrive when they feel supported but not micromanaged. Support them by:
- Encouraging ownership of a project or process
- Reviewing team performance together
- Talking about where they want to grow next
- Keeping communication open and honest
Onboarding Executives: A High-Altitude Year-One Plan
Executive onboarding isn’t just “manager onboarding but more.” It’s fundamentally different. Executives influence culture, strategy, alignment, and organizational health. Their onboarding should reflect that responsibility.
Pre–Day 1: Align Before Arrival
Executives should walk in understanding:
- Their decision-making authority
- High-level goals and major risks
- Key relationships they’ll rely on
- The history of major initiatives (what’s worked, what hasn’t)
First 45–60 Days: Listen Before Leading
Executives don’t need fast action; they need fast understanding. Executives who slow down here tend to move faster later. Support them with:
- A structured listening tour (team, peers, customers, skip-levels)
- Biweekly one-on-ones with other executives
- A deep dive into culture and history
- Clarity around what to focus on immediately vs. later
60-Day Alignment: Turn Insight Into a One-Year Plan
Around the 60-day mark, executives should build and review a one-year plan that outlines:
- Priorities
- Risks
- Team strengths and gaps
- Resource needs
- Cross-functional dependencies
Six Months: Visibility, Culture & Influence
At this point, executives should be shaping direction, not just observing it. This is where their leadership “shows up” across the business.
Encourage them to:
- Seek peer feedback
- Meet with skip-level groups
- Lead visible, consistent communication
- Identify high-potential talent
- Continue coaching
One Year: Long-Term Leadership
By the one-year mark, executives should feel fully part of the business. They should:
- Review their first-year impact
- Refresh their strategy for the next 12–18 months
- Realign with peers and business leaders
- Host quarterly team meetings
The Last Word
At the end of the day, great leaders don’t happen by accident. Instead, they are shaped by the clarity, support, and trust we give them from the very beginning. Thoughtful onboarding isn’t just about completing a checklist; it’s about giving managers and executives a real runway to learn, settle in, and lead with confidence. When we show up for them in those early months with structure, communication, and a genuine investment in their growth, the entire organization feels the impact. A little intention goes a long way, and over time, it helps create the kind of culture we all want to be part of.