An Entrepreneur’s Guide to Management
I have found that an interesting thing happens when your startup forms its feet. As the founder, it’s always been your job to see the road ahead and to share that vision with as many people as possible. You learn to speak tactfully about your business, constantly “selling” the idea to others. You also do a little bit of everything — from the finances to the social media marketing — as your baby grows.
And then, one day, you bring on that first team member. And then your second, and your third. And suddenly, your job changes right before your eyes.
Not only do you continue on this entrepreneurial journey, but you do it as a manager. And then, if you’re crazy enough, as a manager’s manager.
I hear a lot of stories about entrepreneurs who aren’t great managers, and how this step in the startup process can be one of the most difficult. And it’s true: as anyone who’s been through it knows that being a manager requires an entirely different set of skills than being a founder.
I suppose it makes me a bit of a nut, then, to share that for me, being a manager has been one of the most gratifying parts of entrepreneurship that I’ve experienced to date.
It means that suddenly, not only am I crazy about my idea, but I have five other people who are crazy about it, too. We use our mutual energy to support each other and raise each other up, and we dust each other off when things aren’t going as well. We become a family, even though we all telecommute and are actually hundreds — if not thousands — of miles away from each other.
There is absolutely nothing more wonderful, in my opinion, than managing people who truly love their job.
Despite how much I have come to love management, I don’t think the entrepreneur-to-manager jump is talked about enough. We hear all sorts of recommendations about how to make your first hire, but we don’t hear what happens next. And often, as entrepreneurs, we’ve long forgotten these details.
As I grew Wanderful’s team, I spent countless hours digging into the recesses of my brain for management tips. I thought about my old jobs and how they managed their employees. What was my performance review like? What did I appreciate about my manager? What did I wish I had more of?
I searched around on Google for goal-setting templates and other tangible tools. I asked my friend Darren, who works in HR, for tips. And I was lucky to have had some indispensable advice from my executive coach, Paul Corona, while still at Kellogg to keep me on track.
I hope these nuggets of wisdom can save you a bit of time and energy as you grow your own businesses to follow your dreams.
Here’s what I’ve learned.
Give Them Ownership of the Big Picture
I famously talk too much to my team. I tell them everything (after they sign their NDAs, of course). My team knows when we’re struggling, and when we’re cruising. They know what everyone else is working on. But most importantly, they know exactly why we do what we do.
It seems like a no-brainer to emphasize that it’s important for every team member to understand the “why” of your business. But I cannot emphasize enough how much of a difference it makes to actually sit down and explain it. When someone understands the why, it enables the employee to share their input on the what and the how. But without that information, all they can do is deliver what you ask.
As an entrepreneur-turned-manager, I have learned two important things in this regard.
The first is that I often don’t actually know what I want. I know what I want in the long-term, sure. But I don’t know how to get it. The second thing is that you must empower others to help you build the roads to getting what you want. If you don’t, you will waste far too much time taking them down a misleading path, only to back up the whole team and start over again when you realize you made a bad choice.
That’s why every team member must understand your vision as deeply as you understand it yourself. They should understand what you’re trying to achieve, how you’re trying to achieve it, and why it matters. They need all the background they can get, so that they can be positioned to make the best decisions on behalf of you and your company (even if that decision may seem small, like what time they should be posting a picture on Instagram).
So when a new hire starts, how long do you wait before you actually share this big vision?
You don’t wait at all.
Your vision should be the first thing that comes out of your mouth on the very first day of work for your new team member. It makes absolutely no sense for your team member to learn anything until she has the lens through which to view her learnings. Give her all the written information you have about your company. Give her third-party articles, videos, podcasts, everything. Have her review these before you even talk. Then set aside some time to share your vision in detail, and encourage her to ask questions.
Your goal as a manager is to get your team members thinking more deeply about their jobs than you do. As you become a generalist, your team members must be specialists. And if your specialists have the appropriate tools in their proverbial tool belts, they will be in a better position to question you and your assumptions, as well as recommend new courses of action, as you grow this company together.
The second thing you must do with your new hire is make sure that she understands she is part of a family. Whether your company meets in person or online; whether they’re all in one city or spread across the globe, having a strong company culture is absolutely essential to achieving a highly collaborative, creative, critically thinking team.
Encourage your team members to talk with each other, whether or not you are present for those conversations. Have new team members take time to sit down with each individual member of your team and discuss how they can work together and come up with their own solutions.
Have face-to-face time when possible. Especially when your team is still small, find ways for everyone to get to know each other. Plan fun activities and retreats. Compliment your team members in front of the group. Encourage respectful disagreement and productive collaboration.
Be mindful of the example you are setting. You are the one who will ultimately teach your team members how to act with one another.
Do Brain Dumps
When you’re a solopreneur, it’s easy to fall out of the habit of writing things down. That’s because you’re the only person who needs to know that information anyway. I don’t need to write notes about a client and our relationship because I know what our relationship is like. But when you bring on a new hire, you need to find a way to transfer all of that existing information into the mind of someone else. This is where Google Drive becomes really useful.
When I hired my sales manager, one of the first things we did was just a complete brain dump. Her job was to get everything out of my head. We knew that if she left it to me to give her all the information in a nice little package, I’d never get it done. So she would create a spreadsheet, enter in as much information as she could, and then we’d jump on the phone and she’d go through the spreadsheet line by line and ask me to talk about each item. And I would just talk away. Which would remind me of other line items to discuss, which she’d add in as well.
Obviously, this might work differently for different people. Some people might prefer just taking the time to create something and handing it off to their new team members. Others might give someone access to their email inbox and encourage them to dig through it. Whatever your method, make sure you really do set aside some time to transfer information from your brain to your new hire’s. It’ll save you a lot of time and energy later.
When you run a startup, every day is different. Sometimes you’re on the road, or working from cafes, or at home. Sometimes you spend your whole day doing finances, or you divide your day into a number of activities. Even my priorities shift regularly, as a month in startup life feels like a year elsewhere. I might be all about this new activity, and quickly ditch it or make an unexpected adjustment (they do say “fail fast”, anyway).
This is why sharing your vision is important. By allowing your team members to see the ultimate goal, they pivot quickly with you on new ideas.
At the same time, now that you’re managing others, you’ll also want to work in a certain amount of consistency to keep everyone on track.
Start by co-creating with them. Build a set of team values and make sure every team member is on board with it.
After that, encourage each team member to create her own goals. What would she like to achieve in the next year with this position? What are the actions to get her there? What would she like to do to grow professionally, and how can you as their manager help her with this?
Finally, institute regular check-ins. At Wanderful, we have a full team meeting every two weeks, and one-on-one meetings on the alternate weeks. At our first one-on-one, we review our individual goals and schedule a quarterly check-in (akin to what you might call a performance review in some organizations) to make sure we’re still on track. Yet at every meeting, we’ll ensure that our actions are in line with our goals.
Keep these meetings going. Even if you think you don’t have too much to talk about, try to meet anyway. If you find you’re able to end early, end early. Never make the meeting longer than you say it will be. Respect everyone’s time by giving a clear start and end time, and monitor conversations for length. If something merits a follow-up meeting, schedule that for another day.
Let Them Speak First
When we have our team calls, often the first thing I want to do is update them on things I’m working on, or tell them some news from the Wanderful front. But in my opinion, the best thing to do is actually to let your team members speak first. Ask them to give you (and each other) updates on what they’re working on.
This accomplishes a few things. First, it implicitly shows them that what they have to say matters. Their thoughts and questions take priority as they grow as specialists in their field.
Second, it allows them to take ownership of their responsibilities. They’re not blindly following what you ask, but they are responsible for knowing what they should be working on and updating you accordingly. You may be surprised how many of the items on your list get checked off during your team member’s updates. You allow them to take pride in their work and teach them the importance of self-management.
It also strengthens one final point: everyone must use their brain, because you as the founder are not always right.
Share Your Failures
One of the things I can’t stress enough is that, as an entrepreneur, it is not your job to know everything. In some ways, you need to know a little bit about everything, especially when you’re running the whole business on your own, but when you hire people the opportunity to learn and grow opens up.
I hired my first sales lead when I realized that I needed someone better than me to bring in deals for Wanderful. I have learned to survive as a salesperson but definitely still feel I have a lot to learn. In her first week, I had my hands wrapped around this big deal that I was really excited about. The client was excited, I was excited, and after an illuminating phone call I presented my proposal.
After the client received my proposal, I never heard from her again.
I was baffled and a little bit hurt. What did I do wrong? Did I scare this client away? On an afternoon walk with my husband, I shared my concerns with him. My husband had worked in sales before and has one of those magnetic personalities that fills a room. He asked me to share every step of the process of how I presented my sales pitch.
After I finished, he looked at me and gave a long sigh. He then proceeded to list a handful of things that I did wrong, and that in sales you should never, ever do.
For a while I felt pretty miserable about myself. Here I am, hiring a sales person, closing on this deal, only to come back to her with my tail between my legs. I really beat myself up about it. Wasn’t I supposed to be training her? How can I do that if I can’t even show her how to close a deal? How am I going to pay my team now if I can’t even bring on a client?
But instead of hiding from it, we had a long conversation about what I did wrong and what I should have done instead. By losing this deal, we were able to make big adjustments to how we talk with, and present packages to, potential clients, which has only helped us secure new partnerships for the future.
Don’t be afraid to share your failures with your team. That way, you can both learn from the experience and become better in the future.
Share your vision. Work side-by-side with your team to create a plan. Set up regular check-ins. And then, trust them to execute. Let yourself focus on managing, rather than micro-managing, your team. Focus on your own tasks and let them do their job.
Transfer Ownership With Care
When you’re working with a new account manager, make sure to pass along your clients very carefully. Divide your clients into various categories. Are you in regular touch with this client, or have you not talked in a long time? Who can your staff follow up with directly, and who needs to have a few joint calls first so they feel comfortable with their new contact? Are there any clients who you feel you personally should stay in touch with, regardless of how many qualified people you have working for you?
Someone who taught me this through her example was my friend Kathryn who runs a great organization called Unearth the World. We have worked together on a couple of trips for the Wanderful community and she has always been my primary contact.
When Kathryn left for maternity leave, she very carefully transferred me to her colleague. I was impressed with how well she communicated what she was doing, as if I were a delicate egg that she didn’t want to break. First, on a call, she told me that she was bringing on her colleague to help with some things while she was away. Then, we had a dual call together. Only after a few of these did she ask if it was ok if I continued speaking with her colleague while she was away. At every moment of the process, I felt absolutely informed and taken care of, and I was happy to be passed on to make it easier for her.
Have Every Team Member Partake in Interviews
Just as it is important for you to set company culture, it’s important to ensure that each of your team members also contributes to the productive growth of your culture. This contributes to their ability to take ownership of their jobs and their role with your company.
Especially when you’re small, make sure that each team member weighs in on any new additions. Ask them to partake in the interview process, but respect their time. They won’t be able to interview everyone — wait until there are two finalists left and then ask them to weigh in. Give them all the background they need, and make sure they understand what kind of hire you’re looking for. You may be lucky enough to find that their inclinations end up about the same as yours.
I hope that some of these lessons can help you as you grow your own teams and cultures. And I encourage you to share some of the things you’ve learned in the comments below. What are things you have found that help you shift from entrepreneur to entrepreneur-manager? What would you change if you could?