Scaling up a small team in a bootstrapped startup can present some unanticipated challenges. Here are some things to watch out for.
Quick Take: Scaling Up a Small Team
We often work with successful startup founders who start to scale their businesses. They’re moving from a small initial team of people they knew and have worked with. Usually, they start with two to four people, where one may be a cofounder, but the organization has no hierarchy. It’s peer-to-peer with a free exchange of ideas. Sometimes, there’s a contractor, or they may rely on a virtual assistant.
Here are some to manage the challenges that occur as you close deals and add customers
As your team grows, things naturally become more formal. Meetings get bigger, and the dynamics change. Early on, when you’re working closely with peers, you can make suggestions or brainstorm without people taking it as a direct order. It’s understood as part of a back-and-forth process to solve problems. However, as new team members join, they start to see founders “the boss” rather than a peer, which gives your words more weight. This means any criticism you give hits harder for newer team members compared to those who were there from the start. You can’t work in the same way as before.
Ask for feedback. In the early stages, when everyone is working closely together, feedback happens naturally. People will speak up if they think you’re making a mistake. But as the team grows beyond that core group, you need to formally ask for feedback and make it clear you’re open to it. It’s important to document this feedback to show you’re taking it seriously.
Take advantage of newcomers’ perspectives. When you bring in new people, they will see things differently and offer fresh perspectives on how you’re running things. If you dismiss their ideas early on, they’ll stop giving you feedback. If you’re stuck in the mindset of “this is how we’ve always done it,” you won’t get the most out of their input.
Frame a challenge and ask for input before giving your answer. In Japanese culture, senior team members speak last in meetings. This could be a good approach—ask for feedback starting with the less experienced members. Also, make sure to write down and keep track of suggestions so people know they’re being heard. In brainstorming sessions, there will always be some bad ideas, but you need to work through them to get to the good ones or improve on them.
Make the effort to keep everyone appropriately informed. Early on everyone can be involved in any conversation they care to. In a small office they may not have a choice. But at some point everyone cannot be involved in or even informed about everything that’s happening. People can find it difficult to make the right decisions without an understanding of context and priorities. As a founder you are likely have a higher level of understanding–provided you don’t punish people for bringing you bad news. It’s essential you invest time and effort in keeping everyone informed and able to make effective decisions in their area of responsibility.
Increasingly, your job involves making other people productive. I remember a conversation about one founder’s delegation style at a startup I worked at more than three decades ago. “He gives you the impression he could solve the problem he is giving you faster and better than you could but he now has so much to do that he has to offload the less important tasks to someone less capable. He would prefer to control your hands on a keyboard in parallel with his coding but he cannot figure out how. So he is always a little pissed off when he is explaining what he wants you to do.” Don’t be this guy. Take the time to share your view of the situation and connect the dots between the tasks you are delegating and the needs of the team or the startup.
Balance time spent with peers, the people you manage, customers, prospects, and partners. Hold regular one-on-ones with your subordinates where they set the agenda. Compare notes regularly with senior people individually and in executive team meetings or other structured formats. If you are not talking to customers, you can lose touch with critical problems; if you don’t go on sales calls or talk to prospects, you can lose touch with emerging needs. Regular discussions with key people at partner firms will help you maintain your peripheral vision and a “distant early warning system.” Multiple perspectives may conflict but will give you a more holistic perspective on challenges, risks, and opportunities.
Numbers, facts, stories, hopes and fears are all important. Not every meeting should be an email. Spreadsheets and numeric metrics are necessary but not sufficient. When there is an emotional component to a communication–in particular when people are frustrated, angry, or afraid–face to face communication or at least voice communication is essential. Put numbers on key business parameters where possible but a good story can crystallizes an important insight in a way that a spreadsheet or diagram can’t. The flip side is that a room full of people may listen to you tell several stories that are important to you, but if you cannot explain whey they should care you may just be wasting their time.
The handy phrases:
- “What is the problem you are trying to solve?
- “I need your help.”
- “Can you please explain it again in simpler terms,”
- “Can you draw a diagram?”
- “Thank you for your work on this.”
Your Turn: What have you found helpful when you have been part of scaling up a small team? Please leave a comment or drop me an email.
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