5 startup leadership lessons I’ve learned since hiring my first employee

By Heather Wentler


Before Doyenne made our first staffing hire in early 2019, we spent several months creating our employee handbook that we hoped would lay the foundation for a healthy company culture for years to come. 

Our handbook covered things like core values, vacation policy, how day-to-day work is accomplished, and our commitment to diversity, equity, and inclusion. 

We wanted to, as much as possible, avoid the common startup mistake of waiting to define your culture until you have a team of several dozen, and then realizing that your culture already exists and you’ve got a long road of undoing ahead of you. 

But whether you acknowledge it or not, your company already has a culture even if you’re a solo founder. You already have established norms for how you do business and communicate with customers. And no matter what those norms are, bringing in your first hire necessitates a culture shift because you’re introducing a hierarchy and an unequal power dynamic. Even if you claim that there isn’t a hierarchy within your company, your behavior is still the strongest influence on the culture.

Over the last 18 months I’ve learned a lot about hiring and managing. Here are some of my biggest takeaways.

        1. It’s easy to overestimate how much one person can do when you write your first job description.

One of the goals Amy and I had with hiring our first employees in Madison and Milwaukee was to remove ourselves from some of the day-to-day business of the organization so that we could focus on expanding Doyenne to other cities and, eventually, other states. 

We dumped all of the tasks that were distracting us from doing that expansion work into the job description, but we didn’t ask ourselves if it was really feasible for one person to cover the responsibilities that two people had been sharing. 

When you’re making your first hire, it’s hard to gauge how much work is appropriate for one person, because you have no frame of reference other than your own effort, which probably includes many off-the-clock hours. To avoid burning out your first employee immediately, I recommend trimming the responsibilities down to two or three categories with clear objectives.

        2.Your relationships and trust won’t instantly transfer to your employee. 

Much of the work that Amy and I wanted to get off our plate was relationship-based. We had spent five years developing relationships with various stakeholders in the Madison and Milwaukee entrepreneurial ecosystems. We expected that our first hires in both cities would be able to smoothly take our place within those relationships and pick up conversations where we left off. But, as we learned, even when you hire an absolute rock star of an employee, your network will still need some time to develop trust. 

And depending on the kind of work you do and how freely you’ve given out your cell phone number to your customers, it may also take some time to break your customers’ habit of calling and texting you with every question. Establishing those boundaries and transferring contacts takes time and dedication. It can be a delicate dance of making sure the contact feels that you aren’t trying to brush them off, and also transferring the knowledge to the employee of what expectations the clients have from working with the founder or other staff. But every time you, as the founder, step in to “help,” you’re actually creating more work for the employee and taking away their autonomy.

I now have a more realistic expectation around the amount of time it takes for new team members to establish trust with Doyenne’s key partners. Until that employee has established that trust, they won’t be able to operate at the same level of efficiency as whoever was doing that work before (whether that’s me or a previous employee in the same position). 

        3. A flexible schedule only works if you have rigidly defined goals. 

At Doyenne, we close the office for two weeks in the summer and two weeks at the end of the year. In addition to that, we have a flexible schedule that allows employees to take unlimited vacation days and to set their schedules to meet the other demands within their lives outside of work. 

But what we quickly realized after we made our first couple of hires, and especially after going virtual because of a pandemic, is that the goals we had established for our team were not defined well enough to make that policy feasible. The goals need to be framed around making measured progress toward specific accomplishments.

Often, when a startup makes its first hire, founders expect to be able to offload tasks as they come up. But this doesn’t work if the employee is taking a vacation because the founder hasn’t assigned them anything recently. Also, the “offloading unpleasant tasks” approach makes for a pretty miserable job for the employee. Research shows the most satisfying jobs are the ones where employees feel like they have a purpose and they know why their work matters. In my experience, this means having long-term goals and the autonomy to plot a path toward achieving them, not simply doing your boss’s grunt-work.

To make a flexible vacation policy work, you have to check in regularly with your team to come to an agreement about what milestones need to be accomplished by what date so both you and the employee can feel comfortable with them taking time off. This might mean quarterly progress reviews and goal setting, or it might happen through a weekly or bi-weekly team and/or one-on-one meetings to address needs, daily or weekly check-ins, or policies around how the team should use different technologies for communication.

        4.Your default tendency will always be to hire people you’d like to get drinks with, no matter what you say in your employee handbook about your commitment to diversity. 

It’s human nature to want to be around people that you get along with, who remind you of you. But as a leader, this is a tendency you have to consciously battle when making hiring decisions. 

Hiring for “culture fit” is a big trend that can easily backfire if that simply means someone who the founders can imagine getting drinks with. Culture fit is supposed to refer to things like growth mindset, ability to collaborate, willingness to take responsibility for failure, etc. None of these things correlate to whether you drink West Coast IPAs or even whether you drink alcohol at all. 

And too often, when a new hire doesn’t work out for a startup, the tendency is to try to avoid making the same mistake with the next hire. It’s easy to say, “Now I know what kind of person NOT to hire because that person didn’t fit our culture,” instead of saying, “Now I know what needs to change about our culture to include people like the one we just lost.”

        5.To create an inclusive culture, you have to be willing to change yourself first.

Race isn’t the only type of diversity that matters, but in the U.S., it’s the one that founders often have the hardest time adapting to. When White founders hire BIPOC (Black, Indiginious, People of Color), we tend to make a few assumptions: 

The point of creating an inclusive culture is to make sure that all of your employees—regardless of their race, physical abilities, ethnicity, religion, sexual orientation, gender, or any other characteristic that makes them different from the perceived norm—are treated equally and feel equally respected and able to contribute. 

However, actually creating a culture where this is true is difficult. Two false assumptions hamper many founders. 

1) We think we don’t have to adapt our views or ways in which we think to work alongside people with different lived experiences than us. We set the office standard, and our employees should meet what’s already in place.

2) We expect individuals to come to us and tell us when something we or another employee does or say is offensive or problematic. If no one ever says anything, we assume there must not be any problems. 

These assumptions put the burden onto the “othered” staff members’ shoulders to adapt and constantly call out where change needs to be made. This adds to the emotional labor of their position and creates toxic situations. Founders need to instead take responsibility to change their leadership style and set an example for the entire team. 

Recently, a connection told me, “I have an amazing Black woman who would be a great fit for the Doyenne team because she knows how to work with White people.” The statement left me speechless. I recognize the truth of the statement—that despite our efforts to create an inclusive culture, BIPOC are still expected to code switch and adapt within all workspaces—but hearing it made me pause and think, “What continued work do I need to do so that this would no longer be true at Doyenne? But it also reminded me that I need to accept that I am a White woman who has many privileges that I may take for granted. I do need to be called out so I can continue to change and be a true ally for BIPOC. 

We know the research: diverse teams perform better than homogenous teams only when each member of the team feels respected and safe enough to speak up when they have a difference of opinion. Simply saying, “you can always talk to me if you don’t feel included” does not make someone feel safe or included. You have to be proactive and seek out training to become more inclusive.  

Be willing to learn from your mistakes

Hiring is hard. Managing employees is even harder. Communication breaks down at various points in any professional or personal relationship, and you have to figure out how to overcome these barriers, take responsibility while also maintaining professionalism, and figure out ways to move forward. 

Like everything else in your journey as a founder, you have to be willing to forge into the unknown, feel uncomfortable and vulnerable in the process, and learn from your mistakes. But whenever possible, take the shortcut and learn from someone else’s mistakes. Your current and future employees will thank you.