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How I hired a team of 6 without having a clue what I was doing

by Josh Pigford. Last updated on January 26, 2024

Last week I wrote about our experience going from bootstrapped to funded, why it was good for our business and some of the things we’ve learned along the way. I mentioned there were some big shifts for me and one of those shifts was the transition from being a solo entrepreneur to managing a team.

I have 10 years of do-it-yourself mentality to undo, or to at least adjust, and that’s been an interesting process. I’ve moved from a pure maker to more of a manager…an enabler. Instead of doing all the “making”, it’s now my job to make sure my team is well equipped and fully supported to do what they do best and for me to stay out of their way.

So, what are some lessons and tips I’ve learned along the way?

The sooner, the better

You should start building a team as soon as it makes financial sense. I’m technically capable of pulling off the high-level development of things, but I’m not an expert at it.

I quickly found myself in over my head dealing with the huge amount of data we manage and for a couple of months was in a perpetual state of putting out server fires.

Ben, the first person I hired, came in and within a matter of weeks had fixed the large majority of the major issues. I should have hired him months earlier.

Having someone to focus on development freed me up to focus on growing the business, which is a much better use of my time.

Team communication is key

We’re a 100% remote team, covering all four U.S. timezones. We miss out on office chit chat and the little opportunities here and there to throw an idea by someone in passing or to discuss something over lunch.

That means we have to be very intentional about communicating with each other. Even as a team of six it’s easy for people to go a whole week without talking to someone else on the team and at our size we have to try and avoid that.

We use Slack to quickly talk through ideas and questions as well as for the liberal sharing of GIFs…because GIFs = culture. Right?!?!

We also use Sqwiggle for indiviual and team video chats. It shows who’s working at any given time and helps give a bit of a “we’re all here working and making junk happen” feel.

Trust your team’s expertise

I don’t consider myself a micromanager, and I certainly don’t want to be that. But it’s definitely a struggle to let go of something that’s been your “baby” for months and trust that others will want what’s best for it too.

It’s really important to step back and let the people you hired do what they do best. You hired them because they’re experts. They are (hopefully) better than you at the job you hired them for, so quit telling them how to do their job.

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Your role at this point is to steer the ship. To instill in your team the direction things need to head and then step back and let them work.

There’s a ramp up period

Once you start hiring, even if it’s just one or two people, it will take time before the things they’re working on will start to make a major difference in your business.

It’ll take time for everyone to get in step with one another and to start really producing things together that make a big impact.

That’s par for the course.

It’s also something to consider from a financial standpoint. Can you afford for the work they’re doing to not pay off for 3-6 months? If not, you may not be ready to hire.

Equip your team

Every position has different needs. Heck, every person will have different needs, even within the same job. Make sure everyone has what they need to do their job well.

On a granular level, that means answering questions and giving feedback on work as quickly as possible so you aren’t the roadblock.

On a higher level, that’s making sure everyone’s happy. Some of the things we do to help in that department is giving these to everyone:

  • Kindle Paperwhite
  • Unlimited Kindle books
  • Jawbone UP
  • $250/mo “remote stipend” that can be used for anything (phone, internet, food, gym membership)
  • Loose vacation policy

Those are small things, but they can go a long way in making sure people don’t get burnt out.

Give everyone opportunities to speak their mind

You can’t make the assumption that everyone is happy all of the time or that they never have any ideas they want to run by you about how the company & team can be better. There will be times that people are unhappy with certain things and they will have great ideas for how the company and team can be better.

But most people won’t just come out and say those things. You have to give them opportunities to say them and directly ask for that kind of feedback.

We do this via 1-on-1’s every two weeks. Each time I ask specific questions (the actual questions vary week-to-week) to get a better idea of where everyone’s head is at and if there’s anything I can help with.

We even have a bot (MomBot!) to schedule them so they don’t get missed!

Some of the quesitons we ask each time…

  • How’s your work/life balance right now?
  • What’s a recent situation you wish you handled differently?
  • Are you happy with your recent work? Why or why not?
  • Are there any projects you’d really like to work on if you had the chance?
  • Do you feel over-worked, under-worked, or is the workload just right?
  • Do you feel like you’re on the same page with the team as a whole?
  • How could we improve the ways our team works together?
  • Is everyone pulling their weight on the team?
  • What could I do as a manager to make your work easier?
  • Is there any feedback you have for me as a manager?

Honestly, as someone who’s been self-employeed his whole career, a lot of those questions feel icky. Like I’m sitting in a room in my suit with slicked back hair talking down to my minions. But in reality, they work really well for getting feedback.

Learning process

I started hiring barely 8 months ago. I’m still a complete noob at this, but I do think being mindful of the fact that managing a team is very different from building a product goes a long way towards not only a happier, more capable team, but also a better product.

Have you built a team before? What are some things you’ve learned?

Josh Pigford

Josh is most famous as the founder of Baremetrics. However, long before Baremetrics and until today, Josh has been a maker, builder, and entrepreneur. His career set off in 2003 building a pair of link directories, ReallyDumbStuff and ReallyFunArcade. Before he sold those for profits, he had already started his next set of projects. As a design major, he began consulting on web design projects. That company eventually morphed into Sabotage Media, which has been the shell company for many of his projects since. Some of his biggest projects before Baremetrics were TrackThePack, Deck Foundry, PopSurvey, and Temper. The pain points he experienced as PopSurvey and Temper took off were the reason he created Baremetrics. Currently, he's dedicated to Maybe, the OS for your personal finances.