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If you are part of an organization that is growing or experiencing change, odds are you are bringing in, or promoting, new leaders to help with that growth and change. In my observation, many otherwise highly effective leaders struggle to onboard their new hire in a win-win-win for the two of them and the company. According to Gallup, only about 12% of employees strongly agree that their organization does a good job of onboarding.1

Here’s a real example:

After a lengthy search and a hefty recruiting fee, a President hired a new COO. The president was excited, even relieved, that the position was finally filled. She turned her attention back to the rest of her work, relieved to finally have the extra set of hands on the executive team. The COO was excited about the opportunity and jumped into his work, pleasantly surprised by the freedom he was given to do things his own way.

This “everybody’s happy” honeymoon lasted about three months. Then, problems started to surface. The President began hearing word that employees were unhappy under the new COO. She herself was growing impatient at the lack of results she had expected from the COO by now. She was frustrated that she had to return and spend time on this “problem” she had thought was solved three months ago. Likewise, the COO was surprised at the sudden micro-managing and lack of support or feedback from the president.

Lack of direct communication kept the two out of sync. But both were busy, so they kept chugging along. Tension built. Eventually, things blew up.

This doesn’t have to happen.

The Leadership Challenge

Research shows that, more often than not, a new leader’s early failure has less to do with them than with the environment they were dropped into — vague expectations, unclear measures of success, and little help understanding the organization.2 So how do you start well with a new hire and increase the odds of their success?

My advice uses a comparison you will likely understand: onboarding a new leader is a lot like the early years of parenting a child. There are two pathways:

Parenting Style #1: Control, then Freedom. From the beginning, the parent stays close — present, supervising, guiding — while giving the child room to prove himself. As the child demonstrates good behavior and decision-making, the parent gradually pulls back, allowing more and more independence.

Parenting Style #2: Freedom, then (attempted) Control. The parent begins very hands-off, treating the toddler like their best buddy and tolerating bad behavior that ought to be corrected, expecting the child will figure it out on his own. When things finally spin out of control, the parent reasserts authority with a heavy hand. The child, bewildered by the sudden close attention and new restrictions, rebels. This scenario usually ends with frustration and alienation for everyone.

Too often, leaders choose Style #2 with a new hire. Here are three ways in particular hiring bosses give too much freedom at the beginning and then find themselves having to get things back under control.

Mistake #1: Hands-Off. “This person is smart — that’s why I hired her. She’ll figure it out.”

Reality: The new hire may be a smart self-starter, but he is a novice at knowing your expectations, philosophy and desired culture.

Mistake #2: Nice Boss. “I want a good relationship with my new hire. I don’t want to come across as a micromanager.”

Reality: A high level of communication is not micromanaging. Your new hire will actually appreciate the guidance and feedback.

Mistake #3: Too Busy. “I have a mile-long list of responsibilities I’ve been neglecting during this COO search. Other priorities demand my attention right now.”

Reality: Ignoring your responsibilities in the onboarding relationship will create more work for you in the long run.

A little intentionality will put you ahead of almost every boss your new hire has ever worked for.

The Leadership Opportunity

Hiring well is only the first half of the job. The intentional leader leans in early and lets go gradually.

In one study, new hires who connected with their manager or onboarding partner just a few times in their first ninety days were far more likely to feel productive, and those who connected most often were the likeliest of all to get up to speed quickly.3 Another study found organizations that onboard well see far higher retention (as much as 82% higher) and productivity (over 70% higher) from their new people.4 Frequent contact is not micromanagement. It is healthy leadership.

To start well with your new hire, follow these five steps:

1. Agree on a game plan. Have your new hire read and use a resource like The First 90 Days — I routinely recommend this book to senior leaders making transitions. Easy to read, it provides practical strategies and helps set priorities with questions and checklists5.

2. Educate and introduce. As smart as your new hire might be, two biggies they don’t know on Day One are your culture and you. Teach them the unwritten rules — how decisions really get made, what your organization values, where the landmines are. And teach your way of operating — your communication preferences, how you keep score, what will earn your trust6. Then introduce them to the critical relationships they will need.

3. Help them win. Make your expectations explicit — and make them about outcomes, not activities.7 Help your new hire find a few early wins. These will build their credibility with the team and give both of you evidence that things are on track.

4. Get and stay synced. Talk frequently, at least weekly. Debriefing with your new hire daily during the first few weeks is not too often. Have your new hire tell you what he is observing and doing. Give feedback and ask good questions to see how they are processing what they are learning.

5. Guide, but let them do it their way. As your new hire demonstrates good judgment, loosen the reins. Without compromising your principles, give increasing autonomy — and stay open to the possibility that a fresh set of eyes will improve how you do things.

Your task of hiring a new leader is not done the first day they show up for work. Finish your onboarding job well to ensure they begin theirs well and maximize the return on your investment.

The Autopilot Leader vs. The Intentional Leader

Notes

1. Gallup, gallup.com. Gallup reports that only about 12% of employees strongly agree their organization does a great job onboarding new hires.

2. See ExecSpringboard, “Why New Executives Fail,” execspringboard.com, 2026. The underlying point — that a new leader’s early struggles usually reflect the environment and unclear expectations more than the individual — echoes Michael D. Watkins in Harvard Business Review and in The First 90 Days.

3. Onboarding statistics compiled by Appical, “Employee Onboarding Statistics,” appical.com. New hires who connected with their manager or onboarding partner 2–3 times in their first 90 days were far likelier to feel productive (about 73%), rising to roughly 86% at 4–8 contacts and 97% at more than eight.

4. Brandon Hall Group, as widely cited: organizations with a strong onboarding process improve new-hire retention by about 82% and productivity by over 70%. See also SHRM, reporting that employees who go through structured onboarding are markedly more likely to remain after three years, and time-to-productivity research finding that effective onboarding can roughly halve the time a new hire needs to reach full productivity.

5. Another book of the same genre: The New Leader’s 100-Day Action Plan: Take Charge, Build Your Team, and Deliver Better Results Faster, by George B. Bradt, Jayme A. Check, John A. Lawler

6. See related Chapter: __ How to Fast Start with a New Team.

7. See Chapter 11, How to Hire Well, on defining a role by the outcomes it must produce rather than its activities.