I took Maynard Webb’s advice. Here’s what happened

I’ve enjoyed writing this weekly column for three years, and I love when I hear back from founders about how my advice landed and how they are doing. One of the questions

that received a lot of traction this year came from an executive who was looking for more challenges but didn’t want to overextend.

Here’s the original letter and my response, published on June 2, 2021:

I’ve put strong leaders in place and am looking to take on new challenges. My biggest fear is that I’m going to get bored with less to do, but I’m also apprehensive to take on more than I can manage. (I don’t think that the CEO will be keen on the idea of me adding some external endeavors like board seats or investing.) 

-Executive at a crossroads

Dear Executive, 

Congrats on being at this point where you have established that things can run smoothly enough for you to turn to other endeavors. That’s great for the people you’ve empowered and for the freedom it affords you. 

Let’s celebrate that you have climbed the ladder and become successful. But you’ll find that there’s always more to do. At eBay, whenever we got ahead of the curve, there was something else around the corner. Furthermore, just because things are going smoothly now, it doesn’t mean they will stay that way.  In a dynamic fast growth environment, things are always changing.  

Therefore, it might make sense to keep things as they are for the next quarter or two. See how things develop before you decide what else to add. 

As far as your concern about taking on too much, I find that there is usually a way to get it all done. Sometimes, when I start something new it can be overwhelming, but I can’t stay in that zone for long. That pushes me to figure out a way to conquer it, which is usually possible by setting up systems and metrics and bringing on other people when necessary. The irony is that before long, it no longer requires as much from me and I’m looking for new things to do. And so, the cycle continues. 

Finally, just because your boss may not like the idea of you involving yourself in other efforts is not a reason to abandon the idea. If you do need approval, I would recommend sharing the fleshed-out idea and how you will make this a non-issue for your company. (Basically, you must demonstrate that everything you committed to do will still get done.) If you make a good enough case, it will be hard to deny you this request. CEOs need great executives on their team. I bet you have more control than you think. Also, many leaders understand that an extracurricular activity may make you stay longer in your job and will enable you to bring fresh thinking to your everyday work. 

 I enjoyed being able to offer guidance, and I was heartened to hear how this one turned out.

This leader had a discussion with his boss and asked for an exception to the rule about sitting on outside boards. He stressed that he would be able to deftly manage his day job with the outside board work, which would also help him bring new experience and perspective to his role at the company. His request was granted and he’s since found two board roles, one at a late-stage private company and one at a public company. He is enjoying the new learnings that come with his new positions and feeling more fulfilled and more innovative in his executive job.

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