Where Entrepreneurs Go Wrong When Hiring Big Executives

You’re scaling your company and need a few good people to help you excel in areas outside your realm of expertise. It may seem like finding an experienced executive to join your team is the hard part, but the reality is that successfully integrating them and getting the desired outcomes is the real challenge.

Where Entrepreneurs Go Wrong When Hiring Big Executives

If you’re a first-time CEO and you’re several years younger than this new professional, you may think, I hired this person and they are the expert–they’ll know what to do. Please, please, resist this temptation. I’ve known many CEOs who’ve practiced this management approach, and I have yet to see it yield great results.

Your job as a leader is to be inspiring, fair, and honest–and to hold people accountable to doing their best work. If you do that, you will not go wrong. Don’t become intimidated by years of experience, a good reputation, or simple bravado. You’re the boss, and while they may be the domain expert, you need to make sure that they (and your company) are successful.

That requires active discussion and engagement on all fronts. A winning recruiting and onboarding strategy entails a lot of dialogue for alignment around:

  • What does success look like?
  • What is expected of the new executive?
  • What authority level does the new executive have? (What authority do they have to hire? What input should they get before they fire anyone?)
  • What are the expected behaviors? What is the appropriate style for the culture?
  • What do the first ninety days look like?
  • What problems will they want to tackle right away? What should be put on hold?
  • What is the cadence for check-ins? How often will you be meeting?

I’m a fan of codifying the above in a document so that there’s something to reference and check against. People interpret goals and expectations differently, so this exercise is especially important. (I ask the new executive to take the lead and document what we’ve discussed, and then to let me edit it.) I recommend having weekly one on ones.

These meetings also offer an opportunity to provide advice and to solicit input on how you can help them become more successful. If something is bothering you, you are not doing anyone any favors by hiding your concerns. When you do articulate your worries, try to do so in a way that’s constructive and truth seeking, rather than blaming.

A couple of other points:

You hired this person for a reason. You therefore know that something needs to be done differently, so expect that there will be some changes. You just need to be aligned about what they are.

There’s a lot to be discussed and much to be imparted, but don’t forget that listening goes a long way. Any new executive should be reminded of the importance of listening to the team. I recommend soliciting input about what is going well and where improvement is needed.

As mentioned earlier, there is likely to be change, and the current team needs to be forewarned about and accepting of the fact that some things might be done differently under new leadership. If (or, more likely, when) people come to you to complain about the changes, you need to listen, but also route them back to have a transparent discussion with the new executive.

Don’t forget the basics. Do everything in your power to make the new hire feel welcome. Assign someone in their department to show them around the first day. Take them to lunch. If you can’t personally do it, be sure to have someone else on the team take them.

Remember, the reason you hired someone is that you needed a change. Now set up the conditions to implement that and to make them wildly successful. This takes active management. If you wait, it takes even more work. Never expect things to magically get better. The better you onboard and acclimate someone, the faster they will deliver impact and the faster you will all earn the results you are striving to achieve.

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