As a technology leader, how do you approach succession planning?

We did the exercise annually. I always tried to have at least one replacement directly from my team but it wasn’t always possible. We needed to have 3 people named who could take the role immediately 2-3 that could do it in 1-3 years and 1 or more 3+ years out

However when hiring I rarely was able to use the plan because those 3 top people has usually already shifted to something new inside or outside the company

I started the conversation about my transition about a year ago, so we went through the process of making sure we had the right pieces in place before I took a step back from the business. I'm not sure if all transitions happen at that level of planning and length, so it might be slightly different. However, I have mixed feelings about succession planning. You want to make sure you have pieces in place so your day-to-day things continue and your lights don't go out. That's where you want to make sure that the teams that are reporting to you are able to continue without your involvement. When it comes to replacing me as tech leader or CIO, I think a critical factor is what the company is going through. At what stage is it? Oftentimes you don't want to replace the person who's leaving with someone of the same mindset, you want a shift in strategy, a shift in vision. That's a hard one to plan for.

Have folks feel safe. And provide a vision: Here's a north star, it's a little foggy but we're all driving towards it, however you want to carve that path. The way I've always seen it is if I were to leave, win the lottery or get hit by a bus, at least I know all of that would still be standing. The one thing that I can't answer is who will be the one person to rule them all. I don't know if that's me writing myself out and not having enough confidence in myself to do that, it's a bit of self-awareness for me. But in general I never feel bad about leaving, it’s never like, what are the passwords? Or, who's this and where's this project? Things like that were all in good standing. I don't do a great job at succession planning, to be honest with you. Because it's almost like writing your own will. You don't necessarily want to do it but you know you have to because if you don’t, it causes so many other issues. I was not good at filling in those gaps, but I did have outstanding leaders in the pillars.

When I think about succession planning, I think of one of my standout hires who had uncanny communication skills. He was very adept at connecting with the executives, and immediately developed a rapport with everybody that he met. In many respects, that's more than half the battle. You've just got to be able to connect. The second thing is vision. Carving out a good chunk of the organization and letting him own the vision for it and socialize that vision with the executives, get their fingerprints on it to make it a shared experience across the company, was absolutely huge. Personality-wise, he seemed to attract so much talent wherever he went. He was able to quickly bring in a lot of people. It's also an indicator that you might have a problem if you're hiring somebody and there isn't a living soul that they're able to bring into the organization. That is a red flag.

I think most CIOs and most IT leaders fail at succession planning. We get into the role, we're doing the role, and we haven't thought about the next phase and who's coming after us. Many of us have gone into situations where we've grown our teams and yet we are still getting the phone calls. We think, why is this still happening? As much as I'd like to blame executive leaders I do go back to thinking, I probably haven't communicated that well. I haven't positioned someone who works as part of my team in a way that says they are set up for succession.