Coming into your first leadership position can be painful, and mistakes will certainly be made. As Frank Sinatra says, That’s Life!

The good news is that mistakes are only future lessons that help us build and try harder next time around. As they say, rough seas makes a good sailor!

Here four mistakes I made in my first leadership position. Oopsie poopsie!

  1. I agreed to every goal that was given to me by management, even if it wasn’t necessarily realistic or achievable. Then luckily I surpassed those goals, burned myself out, and the same naysayers that doubted me took credit for the outcomes.
  2. I didn’t check references thinking this was done by HR and paid for it. The new hire ended treating others disrespectfully and not generating any true value. I hired someone with a pitiful reputation in the industry, and in the end made me look bad. To top it off, I waited an extra quarter to let them go when it clearly wasn’t working out. If it’s a dud, it’s a dud, and it is good to clean up the mess sooner than later.
  3. I didn’t hire Sales Ops early on. This lead to my Sellers being overworked spending more time gaining leads then getting on introductory calls. Next time I will hire a trinity for each sales pod, a seller, a sales development representative, and a account manager for each to scale successfully with proper support.
  4. I won’t have everyone attend the same events all at once. One seller per event can collect and delegate leads with my help so there isn’t a competition.

Four team pillars that I want to keep in mind daily next time around:

  1. I listen and play back what I am hearing.
  2. I add value.
  3. I have fun. And I don’t feel guilty playing.
  4. I keep it real, not salesy.

What lessons have you learned in your leadership positions and how did it make you a better leader?

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