Why and How to Fill Your Next Leadership Role From Within

There were a significant percentage of leaders at Boomi who were, at least "on paper", unqualified for the job they were put in. Early on at Boomi we adopted a practice of enabling people who take initiative to take the ball and run with it. More times than not this led to their promotion as they got increasing amounts of responsibility. Several people in this category had never managed people before, and in several cases we hired them right out of school. I was definitely in this category too…I was 24 when I co-founded Boomi in 2000, and when we eventually hired really smart engineers, their favorite thing to do was rewrite all the "founder code".

The vast majority of time this practice worked very well, but why? These people had no experience managing people, growing a team, ensuring peak productivity, etc. yet they managed and grew critical pieces of Boomi’s business as we went from $0 to well past mid–8 figure ARR.

What they lacked in Management 101, they made up for with respect. As these leaders were promoted, sure they hadn’t done performance reviews before, or fired someone, or came up with career development plans, but they knew their shit better than anyone on their team. The people that worked for them saw how competent they were in their particular area, and saw how they could learn from them. Think about all the bosses you have had, would you rather have a polished manager, or a first time manager who treats you well that you can learn a ton from?

There was no ego. No "this ain’t my first rodeo" mentality, no one coming in with bias’s from prior companies that may or may not work at Boomi, and for the most part no real agenda other than “getting shit done”. These leaders wanted to learn, they were open minded, and worked hard and achieved great results. And they naturally looked for those same traits in the people they hired. Really cool to watch.

As we grew, in several cases we eventually did hire experienced VP’s (they were great too btw ☺) and had our first-time leaders work for them. How do you think the first-timers reacted? Did they feel threatened? Did they leave? Nope. They just kept doing what they were doing. They learned everything they could from their new bosses, and it made them even better. In most cases they are all now doing the same jobs their former bosses were doing!

So here is what I learned about how best to approach this.

1. It won’t always work, so make it time bound. Not all doers want to be managers once they try it. So when you do the promotion, you both should look at it as a 90 day process, or whatever period of time you feel appropriate. Have the candid conversation up front that you should check in often (weekly or bi-weekly) with each other to see how its going and make sure its a fit for both of you. Just keep this between yourselves though…when you message it internally, don’t put restrictions on the role or call it temporary, because neither of you will get a gauge if it’s working if the team thinks “I may not work for this person in 90 days.” Assume success and announce it like you would any new leader joining the team. And because you had that conversation up front, it will be much less awkward for your leader to return to their former role if it doesn’t work out.
2. Don’t babysit them. Just because its their first time doesn’t mean you can hand hold them. That drags both of you down. Push them into the pool no matter how cold it is ☺. Of course you need to give them what they need to be successful, but it should be them coming to you for help on specific needs vs. you doing any form of micro management. As the one doing the promotion you have to feel like your workload in that area is decreasing, not spent baby sitting a new leader.
3. Pay them for the job. Don’t be cheap - just because they are new leaders doesn’t mean you shouldn’t acknowledge their increased responsibility financially (and via equity). Now many startups are cheap because they have to be, so I am not saying pay market, but pay them more than they were making. You will likely time the increase to happen once the trial period is over - communicate that going in too.
4. Invest in their learning and growth. Obvious for your whole team, but in this case a great option can be to find them a mentor outside the company who has been doing the role they are now doing. So that investment could be time, travel cost, or free coffee for the mentor. Whatever it is, make sure your new leader knows this is important to you and they should prioritize doing it. Many times, because of the attributes I describe above, they either already have a mentor or love the idea and jump on it.

Big hat tip here to all the awesome people I worked with at Boomi, including first time leaders like Mitch Stewart, JJ Ferroni, Ed Macosky, and the Adult Supervision ☺ including Mike West, Bob Moul, Scott Crawford, Kimberly Gress, Diane Ruth, Ralph Hibbs, Sue Vestri, Chris McNabb. There were many more (especially post Dell) so please don’t hate me if I missed you! These folks were my team, my peers, my bosses, and I learned a ton from all of them.