The worst thing a tech founder can hear from employees…
“You’re the best boss I’ve ever had.”
Oh, the pain! So many things go through your head. There’s the inevitable flattery. You like your team. You hired them for a reason, and now you’ve gotten to know them in a real way.
At the same time, there have been performance issues. Some of them have been subtle, pervasive even. You’ve ended up feeling isolated and frustrated on more than one occasion, as though you were the only person taking your business 100% seriously.
You worked so hard to get that “cool boss” status, though, that the last thing you want to do is crack the whip and come clean about what needs to change.
You’re not “just like them”
Are you the boss who’s “too nice?” Do employees look at you as their pal more than as a leader? Happy employees are productive employees, so it’s natural to think of their well-being. But while this is true, it’s also a common justification for tech founders to ignore the need to develop the management skills they haven’t had to flex before.
Yes, managing people is intimidating. It probably doesn’t come to you naturally. However, you are the boss. You’re not “just like them,” so don’t spend energy trying to paint that picture. Being a tech founder—and now a business owner leading a team—you’re responsible for the constructive criticism, accountability, and motivational capacity that make a leader.
How to be a boss and still be an “OK guy/gal”
Motivate yourself first. You’re closer than ever to doing big things with what started as an idea and a few lines of code. Now you’ve gotten as far as running a team. You’re the boss—now go act like it.
Empower your employees to set deadlines…and keep them
Start by empowering your employees to set deadlines they feel are realistic. This gets them to personally (often verbally) commit to when something will be completed, and allows you to play the “nice card” by letting them retain control over what they’re responsible for.
Next, hold them to it. This is the secret sauce to exercising real leadership when deadlines are set. If a task isn’t done by the agreed deadline, ask what happened, ask them to set up the new deadline, and then keep them accountable.
Check in consistently
By checking in consistently on the status of tasks and projects, you’re reminding your team that yes, you are keeping tabs, and yes, there is an expectation that things get done.
There will be that first uncomfortable time that an employee doesn’t have a good answer for you when you ask for status on a specific task. You might walk away feeling awkward, like the “bad” boss, but that discomfort is a necessary force to remind each teammate that commitments are made to be kept.
Checking in also means getting ahead of problems. Don’t wait for employees to make mistakes that could jeopardize their success or yours. If you ask early and often and then see a problem in its early stages, you can offer feedback and coaching to avoid catastrophe later.
The monkey on their back
All that feedback and coaching sounds great, and is undeniably an integral part of great leadership. There is, however, a limit to the help you should provide.
Specifically, you have to be aware of the monkey. When a teammate comes to you with a problem, picture that problem as a monkey on their back. They point to the monkey, they complain about the monkey, they don’t know what to do with it.
Too often, employees come to you with this money and the hope that their boss will keep it. And as tech founders—who are usually idea people more than natural-born leaders, let’s be honest—too often we take the monkey without blinking. If you’ve done this, you probably wanted to be the awesome boss, or felt you could take care of the problem faster or more easily. Or maybe you balked at the idea of your employee stuck in the trenches of this problem, working on it for who-knows-how-long, while other deadlines had to get pushed back.
Whatever you do, when employees come into your office with a monkey on their back, they need to leave with the monkey. Use these conversations as an opportunity to offer ideas, to train and coach. But the monkey is theirs.
“It’s not personal, it’s business”
Oh, the Godfather. In 1972, this phrase hit the big screen and was immediately immortalized by fans.
Even for a tech founder this rings true. What does it mean, exactly? It means being direct is not the same as being rude. After all, it’s just business.
Don’t feel guilty about asking for what you need. Direct requests get direct action. If you over-complicate requests, it’s more likely that the deliverable will miss the mark or take too long.
Direct and clear
Communicating directly also requires communicating clearly. Check for understanding periodically, and leverage those regular check-ins to ensure understanding translates to tasks getting done the way you intended.
For example, plenty of tech founders follow-up on tasks at daily scrum updates. If something isn’t getting done, or is getting done but with a different understanding of what you need, this is your time to stand up and get to the point quickly and clearly.
If you are scare of conflict, here’s how you can handle it
Taking on a more active leadership role implies additional intimidating things, too. Among them, there’s the reality that you will have to face conflict. By keeping people accountable, by regularly checking in, and by spelling out what you need without the adornments of small talk, at some point someone will disagree with you or push back.
To avoid conflict, frame each challenge appropriately. Challenge itself is good because it promotes growth and realignment to new opportunities. All you have to do is set the ground rules for constructive conflict.
For example, some indie businesses use “challenge sessions,” or meetings specifically designed to hash out multiple perspectives on a subject. Each participant has to start with two positive comments before adding in a criticism.
Some of these practices can feel forced, but they help us channel our emotions. And yes, that human, emotional response will play its way into your company at some point, so it’s best to be prepared to handle it while still providing the leadership and company culture you want.
Being less of the “nice guy/gal” doesn’t mean you no longer have compassion for your team. You’re the boss, now, which means you have the responsibility to evaluate each situation and help each employee succeed, and that includes employee satisfaction.
“Helping each employee succeed,” on the other hand, does not mean taking work off their plates. It does not mean being “just like them,” because you aren’t. If you’re running a company, you need to give it structure, and that structure requires leadership.
“You’re the best boss I’ve ever had” can be a bittersweet clue that echoes for weeks in your head. If you’re working for your team instead of leading them, if you’re the oddball “teammate” who, by coincidence, also pays everyone’s salary, don’t waste time expecting results you haven’t pushed for. Start asking for the right things and setting the right expectations. If you want to go deeper, reach out to me today.
