Becoming a Supportive Hard-Ass
Are you too nice? Let me tell you about a kinder, gentler tyrant.
Good Leadership (again)
My first post in this not-frequent-enough newsletter was a description of what I consider evidence of good leadership. tl;dr:
External behaviors of a good leader:
People observe a good leader acting and communicating with high integrity around everyone. There’s no difference in how this leader behaves around their teams, peers, boss, or friends.
People regularly see a good leader demonstrating vulnerability and humility, and others model the same behavior.
People feel comfortable providing feedback directly to a good leader and are willing to provide that feedback in front of other people without fear.
Internal traits that produce these external behaviors:
Self-awareness
Empathy
A Growth Mindset
This isn’t a checklist guide to becoming a leader, of course. It’s just the table stakes, IMO.
But isn’t leadership all about execution?
Well…yes. When I talk to new engineering leaders, I tell them, “Like it or not, companies only care about results. The tools you use to get those results are what separates good leaders from bad leaders.” Perhaps that’s an extreme statement, yet it makes a point. Good companies also care about people's development, a company’s social impact, the company culture, etc. But it’s important to be honest with folks considering leadership, especially in the startup world. Results matter the most. Even companies with the best cultures are going to expect results out of each and every individual.
My mistake early on in my leadership career was to put people above results too frequently. This sometimes meant that I wasn’t holding my people or myself accountable for timely, high-quality delivery. I took some bruises along the way as I learned to develop a growth mindset and adjust my own behaviors to better produce outcomes.
So, the internal traits above provide a foundation for being a good leader, and with those traits, you can learn to help your teams execute.
Introducing the Supportive Hard-Ass
If you’re like me and too people-focused, then let me describe a leadership persona you can develop.
Supportive Hard-Ass
n. A leader who genuinely cares about their people and who also relentlessly holds themselves and their people accountable to growth and execution.
Why is this a “hard-ass?” Because relentlessly holding people accountable means that sometimes you’re not going to be liked and sometimes you must let people go rather than grow them.
What are the beliefs and behaviors of an SHA?
People are important: An SHA knows their people on a personal level, and the people who work for them feel seen, heard, and supported.
Growth is required: An SHA understands each person’s strengths and growth areas. They work with each person to build and execute a professional growth plan.
Execution is measured: An SHA monitors individual and team execution. They make sure each person is consistently getting results, and if not, they ask why not and how they can help.
Accountability is required: An SHA holds each person accountable to commitments. If a person fails to meet a commitment, they talk about what happened and why.
Terminations happen: If a person repeatedly misses commitments, despite getting feedback and support, an SHA exits that person from the company.
At the center of each of these behaviors is adult conversations. Healthy adults are able to have tough, supportive conversations regularly. Adults talk about what’s working and not working. Adults talk about their strengths, weaknesses, and needs.
As a leader, you spend most of your time in conversations, and you must make those conversations matter.
What to keep in balance
At this point, you might say, “Doug…I, too, want to be a supportive, hard-ass. But how do I do it? Sometimes people can’t move fast enough. Sometimes people don’t seem to understand their weaknesses. Sometimes my boss just wants me to fire someone rather than try to grow them.”
Answers to these questions are very situationally dependent, so let me talk about the tradeoffs an SHA has to keep in balance.
Time to learn vs. skills needed now
One of the most difficult balancing acts is figuring out if there is time for someone to learn the required skills to do their job. In startup land, it seems there’s never enough time, which makes this tradeoff particularly challenging. Here are some questions to ask yourself:
Can this person learn quickly through self-study?
Does this person need a mentor, and do we have someone with the time to mentor them?
Is this person capable of gaining the skills needed in the time we need it?
Is this person in the right role?
Sometimes you have a person with good potential, but you don’t have the time or staff to mentor that person. This is usually an indicator that it’s time to part ways.
Individual vs. team
Teams share their successes and failures, and a team is only as good as its most-struggling team member. Here are some questions to ask:
Does the team have the right makeup of skills?
Can the team absorb work while a struggling team member up-levels their skills?
As a manager, am I providing disproportionate support to one team member?
Am I allowing the behavior of a brilliant jerk to poison the team?
Sometimes you have to favor the team over a specific individual.
Process vs. speed
The art of process is to have just enough to get the job done. The processes required for a 1000-person company are vastly different than the processes required for a 10-person company. Your job as a leader is to build the right amount of process.
Is your execution completely chaotic? If so, you probably need more process and structure.
Do you not have visibility on what work is getting done and/or no way to estimate completion? You need more process.
Do you find yourself constantly in meetings and feel that nothing is actually getting accomplished? You may need less or better process.
Do you find team members hiding behind processes as an excuse for not completing work? You may need less or better process, and you likely have an individual performance issue.
Supportive vs. directive
As a leader, most often you are giving your team context and stating the outcomes you want them to achieve, and then you’re supporting them as they make decisions on what to do and how to do it. This is supportive leadership.
Other times you have to call the shots, which means telling people what you want them to do and sometimes how you want them to do it. This is directive leadership, and it can be difficult for leaders who prefer to empower their people.
Is this decision something that you as the leader are uniquely qualified to make? Be directive.
Is there a business reason why you need to dictate a solution, perhaps because you have additional context or because you have to pick the fastest path? Be directive.
Is there someone on your team who knows a domain better than you and is more qualified to specify the what and the how? Be supportive.
Is your team very junior? You might have to be directive more often than supportive.
Do you have time to grow someone? Be supportive.
I think you get the idea. My advice is to ask yourself with each decision whether you should be directive or supportive in that decision.
Being liked vs. being respected
Finally, for healthy people, being liked as a human is important to us. Almost all of us enjoy mutually rewarding and mutually beneficial relationships. But being liked can’t come at the expense of making difficult decisions as a leader. This is perhaps the most difficult learning for a new leader.
I’ll write more about this in a future post, but for now, you should add “being respected” as part of how you want to be perceived as a leader. Leaders who make good, logical, explained decisions that positively impact the most number of people and the business are the leaders people will respect.
Dear Doug,
Thank you for sharing your experience and insightful questions.
With gratitude,
Rodrigo