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Five Tips For Successfully Onboarding New Leaders

Forbes Human Resources Council

Bill Stauffer is a Managing Partner of Flatiron Search Partners. FSP is a boutique executive-search and growth-advisory firm.

With hiring season upon us and many businesses building new teams in a largely remote environment, it seems like a relevant time to discuss an often overlooked (yet critical) part of the hiring process: onboarding. As someone who has built teams internally for high-growth companies and now focuses exclusively on helping best-in-class organizations build their teams, it’s a topic that’s near and dear to me. 

There are many books, articles and blogs devoted to “the first 90 days,” but most are targeted to the employee, not the company. While it’s certainly very much the employee’s responsibility to give it their best, it’s also the responsibility of the hiring manager and the company to ensure they set someone up for success. This takes time, effort, communication and, most importantly, follow-through.

As a hiring manager, I learned to self-reflect if someone failed in the first 90 days: Either I hired the wrong person, or I did not set that person up for success. Often, it was the latter. I decided to build an onboarding checklist to fix this because it’s really the execution that creates the magic, not some secret sauce. I’ve tweaked it over time, and the below represents some of my best learnings. 

1. Communication: I find this often overlooked but so crucial. It’s imperative that an organization knows that a new employee is coming, and when, why and what their part is in ensuring the new employee’s success. You must also explain the “why” to the organization. Why are we adding this role? Why do we need this skill set? Why did we hire this particular person? Why will this combo add value to the business? Why now versus later? Why did we not promote someone internally instead? The more you lean into the why, the more thoughtful and decisive it will feel, and the more accepting employees will be. Don’t make assumptions that people naturally know any of this or restrict the information to a need-to-know list. Gain buy-in from the start.

2. Create a culture of success for new employees: New employees need to be afforded the assumption of innocence until proven guilty. I’ve seen the opposite many times (even at some of the most cultish and successful businesses): New employees are almost hazed to see if they have the desire, intestinal fortitude or entrepreneurial ability to be successful, sink or swim, etc. Make it clear to the organization that onboarding new employees is everyone’s responsibility, that you will be checking with the employee to see who has been helpful, and that the expectation is everyone is involved. Tolerate no hazing. And walk the walk: Support new employees in meetings, on calls and in introductions. Don’t hedge to see if they’re successful prior to doing that. Have the confidence to stick your neck out. You hired the person, after all.

3. Set clear expectations: Force yourself to memorialize what you expect over the first 30/60/90 days. Not just “meet so and so” and “attend this training” — that will set you both up for failure. If it’s learning the business, be clear on how. If it’s developing a plan, be specific on what you expect and when. There should be a very clear road map that you both align on with specific outcomes. Refer to it frequently when you meet (see below). 

4. Meet often: This is the most often overlooked piece and the hardest to stay true to. I believe the easiest way to set a new employee up for success is to ensure they have standing time with you regularly. Even though it can be painful to make the time, when I realized I was canceling or punting these, I made the commitment to meet daily for the first few weeks outside of normal hours. Everyone has their own schedule, but you can always start or finish your day with someone. I recommend daily for the first two weeks, two to three times a week for the next several weeks and thereafter at your normal cadence. And equally important, make sure you have an agenda for the meetings. I start Monday with a discussion of the plan for the week. Tuesday through Thursday are focused on execution, and Friday is a recap of what happened, what didn’t, learnings, etc. In the days when we worked in offices, I would try to ensure one meeting a week was outside the office to mix things up a bit. The most important thing is to have the meetings. Once you start canceling, it will be that much easier for you both to excuse yourselves from the process, which will not yield great results. 

5. Provide rapid feedback and demand the same: Nothing builds trust and a strong working relationship like real-time, honest feedback. There are varying degrees of candor that organizations employ, and we could devote an entire article to the merits of each, but regardless of the level, candor and feedback need to be part of every conversation. If an employee fails within the first 30/60/90 days, it should be no surprise on either side. And if they’re successful, you’ve now built a great working relationship with a foundation in transparency. And this is a two-way street. You want to hear from them about what’s not working, what they need to be successful, etc. Go as far as to ask a new employee for a 360 at the end of their onboarding so you can refine for the go-forward. Be the leader who cares that much.

The above may not seem like rocket science, and it’s (intentionally) not. The real deciding factor will be, like everything else, the execution. With the time pressures we all face, not to mention the remote working conditions in place at the moment, it can be easy to push this to the bottom of the list. Don’t. Find the time. Make the commitment. Own the success or failure, and learn and do better next time. Set an example for the organization, and you won’t be sorry you did. 


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