Will Your Team Scale?

What will break if everything doubles? Fix it while you still have time.

Here’s an exercise I use with founders and CEOs to help them scale their organizations. Imagine everything doubled over night: twice as many customers, twice as many employees, twice as many customer support requests, and so on. Now draw the organization chart.

What does it look like? How many more managers do you need? How many of these managers can come from internal promotions? Which of your leaders will be able to take on the additional work load? Which will be in over their head? 

It’s often a sobering exercise. It forces you to take a clear look at the organization and determine where you have headroom for growth and where you will struggle. Maybe you have leaders who are barely keeping up today. Now that vaguely disconcerting feeling that was percolating in the background is brought front and center. You need to carefully consider who can continue to take on more and who is at the upper limit of their abilities. You need to replace those who are struggling with more experienced leaders who can help you scale to the next stage.

Let’s say you’ve got some homegrown talent that isn’t quite ready to scale but shows good potential. You don’t want to lose them and you’re not ready to replace them. You can take on one project to invest more time coaching them. Make sure you’ve got the time and bandwidth. But you can’t have a whole team of people who are at their upper limit. One is the limit.

Remember, the goal of the exercise is to forces you to confront bottlenecks before they become debilitating. Just because someone was hired as the VP of Sales in a $5m a year company doesn’t mean they’re equipped to do the job when you’re at $50m. If they have a growth mindset and are willing to learn, you might be able to retain them in the organization and bring someone in over them who can continue to develop them. But whatever you do, don’t let any single person limit the growth of your company. 

The reason this exercise works so well is that the idea of doubling is not some far-flung future scenario. Doubling is the goal. Ideally you’ll be doubling (or better) every year for several years.

What’s the Sweet Spot?

As you hire leaders in the company consider the experience the candidates bring. Have they operated at your current scale? Twice the scale? Ten times the scale?

Everyone has a range in which they are most effective. Asking them to do a job outside their range adds risk. The ideal candidate will be slightly over-qualified on their start date, at their sweet spot within two years and ideally continuing to grow in subsequent years. Some people will tap out 3 or 4 years into their tenure and some will amaze you by rising to the occasion and taking on new challenges.

But be careful of hiring the classic big company executive when you’re still in the early stages. Executives used to big company budgets and big company teams are often the least effective in early stage organizations where you need to roll up your sleeves and figure out the playbook yourself.

Everything is Broken

In startups, things are always breaking. Customers use the product in ways you haven’t tested. They find the limits and then push even harder. They want things you haven’t built yet at a scale you haven’t anticipated. Will it work? Well, let’s find out! 

And you’re often figuring out things as you go. Naturally, things break routinely. So it’s good to build a culture that is attuned to what’s at risk of breaking in order to act as an early warning system. I’ve often had regular executive team meeting agenda items on “Hot customers” (e.g. at risk of blowing up) and more generally “What’s about to break?” whether systems, teams or processes. 

By making these topics into regularly scheduled agenda items, you’re lowering the threshold for sharing potential bad news. Of course, the goal isn’t just to report on problems, but to foster a bias toward action before things blow up. Ideally you’re brainstorming solutions within the meeting, assigning action items and, as we used to say at Gatsby, “making moves.” 

That might entail assigning a senior engineer to work with a customer, coming up with new lead generation campaigns mid-way through a risky quarter, or cutting features to make a challenging ship date. Almost any action is better than “let’s wait and see” which is what happens in most large companies. 

Problems Compound Quickly 

The reason you want to cultivate this approach is that in a high growth startup, small problems left unattended become big problems fairly quickly. As problems arise, you want to add just enough systems and processes to reduce further chaos, but not so much that you constrain the speed at which the company operates. It’s a delicate balance that you won’t always get right. You might not be able to totally eliminate every problem, but if you can find ways to make modest tactical improvements these can offset the risk of problems compounding over time.

Let’s say you’ve noticed that one of the top support issues stems from overly complex configuration required to integrate with a related product. Left unattended, the more customers you have, the bigger the support burden. 

The ideal solution would be to fix the problem “upstream” from support, meaning the solution gets implemented by Engineering so it’s no longer a problem for support. But Engineering might be busy with new features and might not feel the urgency of improving something that is only slightly broken. Or it might be that the real difficulty of configuring the integration has to do with the complexity of the system you’re integrating with.

Even if you can’t completely fix the problem, can you probably come up with at least a few ways to make the problem less severe. You might write a tech support article that helps customers with common configuration problems and make it prominent on the web site, create a video tutorial that walks people through the most common configurations, train the support team on how to diagnose the issue faster, or get the system engineers to help customers with the configuration when they’re doing a proof of concept. While none of these solutions is quite as good as an upstream product fix, they can alleviate some of the burden. 

Alternatively, you could establish a quality task force with executives from engineering and customer success reviewing every feature in development to ensure that there’s an increased level of testing of new integrations before they are rolled out to customers. That might make sense in a larger company, but it’s probably overkill in a startup. A tactical “good enough” solution may be all you need. 

That said, not every problem is worth worrying about. Sometimes, in order to focus on your top initiatives, you need to relegate some problems to the back burner. When you do so, it should be a conscious decision and clearly communicated. Otherwise, employees tend to continue with the work they’ve been doing.

For example, when a company is pivoting to a new strategy, you will need to reassign people to new products and initiatives. It’s often not as easy as simply turning off old systems and moving on. You may still have customer obligations and revenue on the line. In such a case, you may need to limit investment in your old products, perhaps to minimal bug fixing for a period of time. 

You’ll need to communicate that repeatedly, to teams, to leaders and to individual employees to make sure they understand the implications. You’ll need to help them reshape their work to focus on the top priority initiatives and make sure that they stop working on other things. In my experience, while everyone understands when there’s a priority shift, people still need some coaxing to change their day-to-day behavior. Additionally, you need to absolve them of feeling about about neglecting low-priority items so that they can move guilt-free to the new priority.

There is risk any time you de-prioritize something, but by making a conscious decision and reinforcing the priorities, you can make the change a little less painful.

At Duo Security, Chester, the VP of Engineering and I created a band that played at company events. One of the songs we used to play was Bob Dylan’s “Everything is Broken.” It captured the spirit of working in a fast paced startup.