Never Have the “What Would It Take to Keep You Here?” Conversation

As a CEO, many of the scariest days I’ve faced have been those when a critical member of our team told us they were leaving the company. Your heart sinks. Your mind races. Your pulse pounds. Everything else fades into the background. On startup teams of 5-50 people, a team member lost is almost always a single point of failure exposed.

(via alan_sailer on Flickr)

As we’ve scaled at Moz, there have been fewer and fewer single points of failure. The big ones are at the executive level, and we recently made a pre-emptive strike that I hope can be helpful, and is certainly worth sharing.

Our VP of Marketing, Jamie and our VP of Product, Adam, have both been with the company for several years, and both have done remarkably well scaling through our early stage trials and tribulations to today. We had a board meeting in July, where I was asked to think about the executive team’s future, and I sent the following email soon after:

Jamie and I had talked about this many months before – the idea that most companies don’t promote their best people until/unless they think there’s a risk that they’ll leave or be poached. I hate that mentality, but I’ve been guilty of it all the same. We had a very strong contributor on our team receive a job offer earlier this year and worked to keep them on the team (thankfully successfully). But, that’s the reverse of how the process should work.

If a team member is doing great work, and you know today that you’d give them a promotion/raise/increased responsibility/more people on their team/whatever in order to keep them there if a competing offer came in, don’t wait for that offer! Do it today. The goodwill you’ll build will far outweigh the costs associated with playing the “will they get poached” roulette. And what’s more, if and when that roulette comes up with their departing number, what you would have offered won’t be enough to keep them on board. A culture where great people are rewarded when they’ve earned it vs. when you’re threatened is going to retain top talent far better than the reverse.

When you’re a small, early-stage startup, this can feel dauntingly impossible. I know it did for me. We were strapped for cash, and that prevents a lot of the pre-emptive strike possibilities. Regardless, it’s still worth sitting down with that team member who isn’t yet at risk but for whom you’d jump through all the hoops you could to keep and having this conversation:

Manager: I just want to let you know that we’re amazed and impressed with your work. We love having you on the team. It’s a privilege to have you here.

Team Member: Whoa. Thanks.

Manager: I want to do more than express positive sentiments, though. If, tomorrow, you came to me and said “dude, I’ve got a competing offer that’s really compelling,” we would do everything in our power to keep you here. As you know, we don’t have a ton of financial resources, but I’d much rather say, today, is there something you need or want in your job that we CAN provide, that would make you less likely to consider another position elsewhere?

Team Member: Umm… I don’t know. Maybe a title bump? Or a vacation this summer? Let me think about it.

Manager: Awesome. Please do, and let me know. We’d rather be preemptive and reward the effort you’re putting in than try to play the “can we match this offer” game 3, 6 or 12 months from now. And heck, you’ve earned it.

Obviously, this is a fictionalized dialogue, but you get the idea. Sometimes, just the conversation alone will help prevent that gut-wrenching day when a key engineer/marketer/bizdev guy/salesperson/manager/etc. comes to you with two weeks notice.