On Leadership and Culture

The culture of any organization is shaped by the worst behavior the leader is willing to tolerate — Gruenter and Whitacker

Leadership can broadly be distilled down to two essential things: influence and expectations. Entire books have been written on each of those topics. There is depth and plenty of surface area to explore in each. For now, we will simply say that ‘influence’ is the ability to open people to ideas, conclusions, or directions they otherwise might not have reached, and ‘expectations’ is helping people have a standard of performance and building the accountability to achieve it.

The unfortunate reality of the tech industry is that it lacks quality leadership as the rule, not the exception.

Culture, by nature, is harder to define and no simple blog definition will satisfy everyone. Even so, a useful framing for culture in a group (company, division, department, or team) is the collective actions, habits, behaviours, and reactions of everyone working in that group.

Leaders are accountable for the culture of their group. Said another way, the cultural brokenness of a group can in almost all cases be traced directly to poor leadership, either past or current. If we explore culture as programmable AI, we know that given some semi-sophisticated and consistent data, a quality ML system will produce good output. Give it garbage input, random bits, with some sloppy rules and you get out about what you would expect in that case. Culture is the output and leadership is the input + AI. One cannot expect good output from poor input or broken rules.

Leaders need to set the tone, direction, and boundaries if they care about healthy culture. And this is the crux: you have to care about culture. Good culture doesn’t just happen. Culture is messy. It’s hard to define, it wants to entropy or run off in alternate directions while you aren’t looking. If you don’t care about culture now, at some point you will, for all the wrong reasons. I urge leaders to care about the little details of culture early and do it on their time frame when they want to, not when they are forced to.

Call to action

Here are some simple actions to impact culture via leadership now.

1. Values — Have, publish, and reinforce your values
2. Expectations — set and be consistent in your expectations
3. Behaviours — Reward positive behaviours, stop negative behaviours, remove behaviours if necessary (and early). Make sure both positive and negative behaviours can be traced back to values
4. Live the example — Be what you want the org to be. Always. Require yourself to be the high bar, not the low bar. Embody your values
5. Take feedback seriously — Listen for themes, correct when needed
6. Listen more than you talk — Leading starts with listening, a lot
7. Learn via listening — Listening leads to learning
8. Stay positive, always — Be solution oriented, look for the good, re-frame and avoid negative spirals.
9. Repeat — This list never ends, it’s a loop

Ultimately the culture of a company is defined by the CEO and allowed to continue by the action/in-action of the company’s board (if they have one). It’s reinforced by folks brought into the org or put into place by the CEO and eventually other senior leaders or managers. However there are many leaders in an org and all of them are also accountable for the culture of their group. Yes, it would be hard to fight a toxic corporate culture, though it’s possible to be the lost island of positive culture in a sea of toxicity. It’s hard work and requires great leadership, but it’s possible.

It’s also possible to have an amazing culture from the top and a group or two within that is not up to the corporate standard. Both scenarios exist. However it’s much more rare to see good local culture in a bad macro culture org. Culture is contagious, both good and bad.

Closing thoughts

Leaders have the ability to shape culture in amazing and subtle ways. If you routinely ignore your test suites, it becomes a part of your culture. Is that what you want? If you allow passive-aggressive comments in your pull requests, that becomes part of your culture. Is that what you want? If you allow a co-worker to verbally attack or insult someone else in front of their peers in a meeting, how you handle that influences culture. And if you happen to allow systematic harassment of any kind, it becomes part of your culture. You don’t want that. Fix it. Better yet, stop it before it starts. Be a leader. Care about your culture. It’s literally your job.

Postscript — Nuts and Bolts of Leadership and Culture

I wanted to keep the above short and consumable. There is much more to be said on the topic and I thought it important to add a slight more in-depth, yet still too short, postscript so as to not get lost in a follow-up post. Even so, this postscript is barely scratches the surface.

Culture just is

You cannot ignore culture. Culture in your group or company is a thing even if you never give it a second thought. Every place has a culture. If it wasn't intentionally created, it will simply grow organically and without direction. With luck your culture could grow into something amazing, or more likely, devolves into something toxic. Recognizing and intentionally doing the important work is an core characteristic of leadership. To intentionally craft culture, start by establishing your organizational values.

Further, define success early and marry it with values to achieve success. Doing so allows you to build a sustainable culture and have success with it. Many times I’ve seen companies with toxic work cultures that are lauded as successful because of financial achievements. While companies that measure success purely in terms of profits or valuation often achieve short term goals quickly, their neglect of culture results in an organization with a shaky foundation that will threaten their long term financial goals.

There is no doubt that long term outcomes benefit from culture. I argue that even short term outcomes benefit from culture. Why? Sustainability, even in the short term.

Culture as reputation

Ours is a small industry. Reputations matter in a variety of ways. At the end of the day, almost all decisions come down to a few simple things: risk, reward, and trust.

We all have a list of companies, based on reputation, that we would never work for. We also have a list of companies, based on reputation, that we might consider but it would cost a lot more to actually make the move. And we have some we would take market or maybe even less than market, at a drop of the hat to be part of.

What we are doing is weighing the risk/reward with how much we trust the company and what we think we are getting into. It’s quite simple. A toxic corporate culture is going to cost you money, talent, and opportunities.

Leadership, if they aren’t asleep at the wheel, know this inside and out and should be working to create a place that attracts the type of talent the company needs and wants.

Culture early

If you are starting a company or group, keep culture in mind from the jump. Work on your values, write them down. Be intentional and explicit about performance. Be authentic with people. Review your progress, gaps and vulnerabilities on a regular basis. Repeat as you grow. Change where needed. Discard what no longer works. Keep getting better.

Turning a Ship — How to change culture

Books can be written on this. However, broad strokes culture can be changed with a few key things (not an exhaustive set, obviously)

1. Values — Be explicit in who and what you are
2. Standard of Performance — Have a standard of performance
3. Expectations — Hold people accountable to your values and standard of performance
4. Coaching/mentoring/training — Invest in your people
5. Change — Make small changes (people, process, organization, projects) to get momentum, big changes (people, mission, organization) to swing directions and set tone
6. Time — Changing culture takes time. The larger you are, the longer it is

Culture at scale

If you didn’t start early, culture at scale is going to be a nightmare. It will be (extremely) slow to change, cause churn, and will be a period of unease for folks making the transition.

But it’s also possible to do.

And it’s worth it still.

At scale, culture is about leading by example, values (always values), standards of performance, accountability, and middle/line management. At scale, middle/line management are the most important cultural leaders in a company. It is literally where culture is made or broken.

For this reason it’s critically important to hire, train, educate and mentor your middle/line managers well. It’s also critically important you set, maintain, and enforce a standard of performance with your managers. This means, among the harder parts of leadership, letting people go who do not fit or do not want to fit.

Further, who you ask to become managers will signal to others what you implicitly value in leadership. It is a cultural signal. Take this seriously and remember your values. A few bad managers can sink an entire org.

Final Thought

Leadership is hard. And we have a lack of good leaders (never mind great leaders) which makes it even harder. We have few examples to hold up as true inspirations.

For all the leaders and future leaders out there, here’s something I very much want us all to take to heart: We must earn the right every day to continue to do the job we were given. Our job is in service to our employees and our organizations. How we react to this will dictate if we are good or bad leaders. Good leaders take it as their responsibility to care for the people, the product(s) and the organization (department, company etc) at the same time. Achieving this balance is what true leaders do; doing it effectively makes a leader great. Any manager can be revenue driven and work people to death. Any manager can create a culture of comfort and get nothing done. Any manager can create an ‘us v them’ attitude for departments or divisions. Any manager can can foster an entitled or political or conniving or fearful environment. None of this is hard. It’s quite easy. These are sadly what we see to often in our industry.

Leaders create cultures that welcome high achievers of all types, set standards of performance, and meaningful missions. And do this in a way that makes people feel valued, safe, and included. Leadership is guiding organizations to this place with intent and purpose. Leadership is focusing on what matters and helping others do the same. All this leads the culture of your organization. Culture starts with leadership.