The Uncomfortable Challenge of Topgrading Your Startup’s Team

If things go well at your startup, there will inevitably be a point where the business is growing ahead of the team’s abilities. Engineers will find themselves facing architectural, scaling, and complexity issues they’ve never dealt with before. Marketers will discover their historical strengths dwarfed by the quantity and complexity of different customer acquisition channels and the huge challenges of attribution modeling, predictive investments, and trying to get more done on a larger team. Product folks, operations team members, customer service reps, salespeople, etc. will all face the same thing.

(via Matija on Flickr)

But, it’s managers who will have the roughest time with topgrading for two reasons. One – they need to navigate the very tricky waters of bringing new talent on board while maintaining the delicate balance of team dynamics. Two – when their own skills aren’t up to the challenges (as mine frequently haven’t been), it’s even harder to find ways to bring in folks with the right skills/experience without hurting culture and/or morale than with individual contributors.

Topgrading has an ugly sound to it.  The natural jump for many is to think “my manager/CEO doesn’t think I’m up to the task, so they have to bring in someone else to do my job.” For that manager/CEO, the thought process hopefully looks more like “Fred’s doing a great job at X and Y, but Z isn’t a strength and we need to do Z. We’re going to have to recruit some help.” This conflict sucks, but it can be avoided with good process and a ton of empathy to how all those affected might feel.

I’ve seen it argued that when a startup team’s abilities aren’t up to the challenges ahead, the right course is to upgrade those skills, not add new, more seasoned members to the startup. This can work, and in some cases it does. But in my experience, it’s a solution only about half the time – the other half, it has to, at least, be combined with bringing in external talent to help.

To be clear, when I say “topgrading,” I don’t just mean bringing in new, more experienced talent who will be in a higher position than existing team members. In fact, as I’ll talk about below, I strongly prefer adding peers who’ve “been there/done that” and are being added to because we don’t want to experience all the pain of doing something the first time without guidance. Sometimes, though, topgrading does mean bringing in that “top tier” style talent that your startup couldn’t afford until now.

Over the course of SEOmoz, we’ve had to do this numerous times on various teams and for different roles. The process usually goes something like this:

  1. Either myself or another member of the executive team feels a tactical, strategic or management need on the team (usually because of some new way we’re growing or new thing we’re doing)
  2. We spend lots of time first working to bolster the missing skills – through mentorship, training, more-bite-sized projects, etc.
  3. Often, #2 works and things progress forward. When they don’t, we need to make some decisions about the team or individual.
  4. Those decisions start by asking a few critical, probing questions:
    • Is this/are these the right people for this project/team moving forward? If not, what else can we assign to them that will flex the skill muscles they’ve got?
    • Do we need to topgrade from outside the company, or is someone else the right person/people for this job?
    • Does the new person’s title/role/responsibility have an inherent, dramatic need to be senior to the current team member(s)? If that need isn’t extreme, hire for a peer.
    • How can we manage this transition in an empathetic way that builds team morale rather than hurting it?
  5. If the determination’s made that we need to topgrade externally, it’s our responsibility to work hard with the team member(s) to make sure they understand all the inputs to the decision and agree with them. Sometimes, this takes a few weeks or even a couple months, but it’s worth it. Nothing demoralizes managers and teams like an executive decision they don’t agree with that directly affects their role and scope.
  6. The recruiting process starts with the team – hopefully someone there has a referral or two. No matter where a candidate is sourced, it’s the team making the decision on who they want to hire. When we added Anthony as CTO in December, it was a lengthy, 100+ day search to find him, but he had nearly unanimous buy-in from the engineering group and completely unanimous approval from the exec team and managers on other teams.
This process works best when the team member(s) themselves institutes the process. For example, our former CTO Jeff Pollard came to me in 2008 and said he didn’t believe his abilities were up to leading the engineering group given the challenges we faced. That action impressed me tremendously and I’ve brought it up with high praise for Jeff ever since. He’s an amazing guy who made a hard choice to step down from his role and bring in outside help. It was a tough period, but an outstanding illustration of how this process can go well.

The topgrading exercise is much harder when the team member(s) don’t see and feel the need, and in fact, I’d argue that if they don’t, there should be more conversations and trials of the existing group (perhaps in innovative ways). The very last thing a manager should do is to force a new person into a hostile environment that won’t embrace them. It’s a recipe for disaster.

At the most recent SEOmoz allhands meeting, I noted that topgrading would become a priority for us over the next 6 months. It’s already beginning with a number of new folks on engineering, product, marketing and in some strategic areas as well (e.g. Peter Bray from Followerwonk leading some social product strategy on Adam’s team). As this process roles out, I’m sure we’ll have some tough, emotional meetings. A few things will make those go easier I hope:

  • Buy-in from the teams and individuals affected, or in some cases, demand directly from them (my favorite!)
  • Very few cases where we need to give senior titles/roles to new talent on the team
  • Knowledge from existing team members that topgrading is in their best interests from both a growth/learning perspective and a financial one (stock option grants always start larger for earlier employees and get smaller over time, and strike prices go up, too, hence earlier folks have great monetary reasons to want the company to succeed in addition to all the other ones)
  • A culture of humility and empathy from all sides – execs, managers and individual contributors
  • Natural excitement when new people who can make us better join the team (at some point, I’ll try to share a few allstaff email threads about people joining the company – they’re super fun and often inspiring)

Topgrading isn’t always the right thing to do, but resistance to it based on ego/emotion is certainly worse. I just hope that as we grow, we continue to remember the lessons of our past and embrace empathy and humility above all. If we do that, I think we’re going to build a team that will make all of us better.

p.s. Joe Kraus has a great post on Techcrunch this morning about topgrading the CEO role specifically.