Hiring Managers

I separate management into two components: supervision and leadership.

• A supervisor is someone who approves vacation time, gives reviews, and decides on salary increases. They basically handle the nuts and bolts.
• A leader—like a tech lead or a development lead—is someone who gives technical guidance, mentorship, seniority, and direction.

A manager is a person who supervises and leads. In a lot of companies, especially in the early days, that role is divided.

At Drip, my cofounder Derrick led our team when it came to technical guidance and code review, but the developers reported to me.

Derrick didn’t need to get bogged down with scheduling vacation time or health benefits—that would have been a waste of his skill set, and I didn’t want him burning cycles learning management when there were features to build. So those supervisory decisions came to me.

You can—and should—hire or promote roles like development lead or customer success lead early to keep every decision from falling back on you. Even before you have the budget to hire a full-blown manager, you will likely find stand-out folks you trust to make decisions for a particular project or department. If you don’t find leads early, you will eventually find yourself overwhelmed with the volume of questions that come back to you because you haven’t put the proper expertise in place.

If everyone who works for you is a task-level thinker (see sidebar), it places a tremendous burden on you as the founder. As you grow and transform from a product into a business, usually in the $20,000 to $40,000 MRR range, it’s time to consider bringing some project-level or owner-level thinkers onto your team.

Not only will this remove stress from your life, but it will also help your team move faster because they don’t need to wait on you for every decision. And if you plan to sell the company at some point, the less the business relies on you, the better terms you’re likely to receive.

When you’re just starting out, you won’t have the budget to hire a manager. It depends on several factors, but I usually recommend finding leads once you have two or three people in the same department and finding a manager once you have four or five people in the same department.

You can stretch this, but it will take a toll on you. It takes up too much of your time if you’re managing twelve direct reports well (e.g., holding weekly or monthly one-on-one meetings, working on career development).

Usually, founders let it go for too long and then start managing their team poorly because they are pulled in too many directions. This can work for a while, but it will eventually lead to poor results or folks leaving your company.

Keep in mind that your first management hires must also be individual contributors. You’ll want to find someone who can manage and develop. Or manage and do customer support or write documentation or work on strategy.

Promoting managers from within can be a good way to go if you have someone ready to move from task-level to project-level. In this case, you take that promising tech lead or head of customer success and train them to run one-on-ones, evaluate for raises, approve vacation time, and—most importantly—give both positive and negative feedback.

Just because someone is a good lead doesn’t mean they will be a good manager. Not everyone has supervisory skills or the desire to learn them. If you hired your most senior developer because of their ninja coding skills, it doesn’t make sense to bog them down managing time-off requests and answering questions about health insurance.

I find that people who’ve had a good manager in the past tend to have a leg up when it comes to being a good manager themselves. The problem is that many bootstrapped founders have never had a “real job” inside a bigger company. They haven’t experienced a range of managers or aren’t familiar with office politics, so they don’t develop a mental model of managing a team well.

One of the more challenging things about becoming a manager is learning to give negative (constructive) feedback. Most people are nice, and most of us don’t like conflict. It’s not fun to have to tell someone they dropped the ball—but it is a necessary skill to learn to help your team members grow and keep the company culture from slipping into mediocrity.

My rule is to praise in public and correct in private. If I’m going to tell someone they screwed up, it’ll be in a one-on-one meeting and never in front of someone who wasn’t involved. Team meetings are for giving out props to team members who are doing a great job, not tearing someone down for a mistake.

Giving both positive and negative feedback builds trust, which is the most important part of being a good manager.

Your team members need to trust that you’ll be fair. That you’ll listen to them. That you’ll make good decisions. That you’ll take the fall instead of throwing them under the bus when things go wrong—because if someone below you makes a mistake, that ultimately falls on you.

They also need to trust that you’ll tell them the truth, even if the news is not good.

One company I worked at had a problem where the managers were too nice. Eventually when they had to let someone go, that person was shocked because no one had ever told them something was wrong. Of course, they then spoke with old coworkers via a back channel, word spread around the company, and suddenly everyone was wondering if they were next. The trust was broken.