All Articles Leadership Management What's one people-management mistake you wish you could go back in time and fix?

What’s one people-management mistake you wish you could go back in time and fix?

4 min read


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1. Eliminating toxic team members
I wish I could go back in time and eliminate toxic team members from the moment they became toxic. I spent too much time (and let the rest of the team suffer too much) trying to fix their attitude over a number of months when the best answer for the team as a whole was to just let them go and move on healthily. — Brennan White, Watchtower

2. Pushing people in wrong directions

In an attempt to generate business quickly, I tried to get my CFOs to take a more active role in business development. Suffice to say, most of these financial professionals didn’t have real sales interest or skills, so this didn’t go over so well. Since then, I’ve focused on identifying my team’s strengths and allowing them to capitalize on these, rather than fulfill roles they aren’t suited for. — David Ehrenberg, Early Growth Financial Services

3. Trusting the wrong people

Trust is something that has to be earned, but when you are a startup, everything moves quickly. You are trying to find investors, employees and customers, and you have to assess people in an instant. Sometimes those assessments are wrong. Knowing what I know now, I can see who to trust and who to avoid. — Ty Morse, Songwhale

4. Delaying the tough decisions

You’re the boss for a reason. Take on the big, tough decisions first, and make sure all responsibility for the results falls on you. You’ll simultaneously earn trust from your team and remove obstacles for your company. — Neil Thanedar, LabDoor

5. Expecting others to be just like me

When I first started managing, I looked down upon direct reports who didn’t have the same skills and talents as I have. Now I realize that the best subordinates have strengths in vastly different areas; this is what makes us a well-rounded team. I wish I could go back and be less critical and more tolerant. — Alexandra Levit, Inspiration at Work

6. Minimizing the importance of results

With my first several hires, I focused on finding someone who could handle work in exactly the way I would do it myself. In reality, it’s rare that replicating a process exactly is necessary. Rather, you just want the end result. It took me far too long to recalibrate toward getting the right results out of my team. — Thursday Bram, Hyper Modern Consulting

7. Assuming too much

Whether it is communication to a client, how to format e-mails or something as small as answering the phone, I wish I could go back and take back my assumption that new employees would just “get it” without any guidance. Assuming caused headaches and confusion not only from a management standpoint, but also for the employees. We now treat each new employee as a blank slate who is ready to learn! — Kim Kaupe, ZinePak

8. Not holding people accountable

I always try to recruit self-starters who “just get things done.” Highly capable people like this hate to be micromanaged, and I usually oblige. Early on, I would be reticent about having them clearly articulate and hit goals. I just assumed they’d get things done on their own. Even high performers can benefit from a little structure. I wish I had implemented this earlier. — Adam Lieb, Duxter

9. Overvaluing industry experience when hiring

Don’t overvalue someone with “industry experience.” It means nothing if that experience is with a bad company or didn’t result in strong performance. What matters is results. Experience isn’t an inherently positive word. Someone can have years of what I now see as “bad experience.” This will make them stubborn, closed-minded and tough to work with. — Phil Dumontet, DASHED

10. Hiring friends

Don’t hire your friends just because you like them. Your judgment about the person’s business talents could be clouded by your existing friendship. Along those same lines, don’t become best friends with anyone who works for you unless you’re thinking of making that person a partner one day. The ability to separate business and personal relationships is vital for employer/employee management. — Robby Hill, HillSouth