3 leaders on balancing bottom-up leadership

An age old question leaders face is how to create new leaders within their organization, ones that could take over the reins someday. Today’s organizations have never been more complex, nor have there ever been more moving parts involved with creating software products. Structures vary in shape and size, each team morphing and sharing responsibilities as opportunities and challenges arise.

Further complicating the organizational structure of teams is COVID-19. While immediately life altering, it will also create lasting changes in how we think about remote work, responsibility and leadership. One thing is clear—whether planned or not, everyone has more autonomy over their own work, making it even more critical to foster bottom-up leadership within a team. We recently spoke with three senior leaders, Heidi Helfand, the author of Dynamic Reteaming: The Art & Wisdom of Changing Teams and director of R&D, excellence at Procore Technologies; Christopher Logan, senior manager of solutions architecture, ISV at Amazon Web Services; and Jonathan Rayback, VP of engineering at Evernym about how they personally think through bottom-up leadership and the tactics and methodologies they utilize in their organizations. 

Author of Dynamic Reteaming. Director of R&D, Excellence at Procore Technologies

Heidi Helfand

Senior Manager of Solutions Architecture, ISV at Amazon Web Services (AWS)

Christopher Logan

Vice President Engineering at Evernym

Jonathan Rayback

How do you balance growing others and a business at the same time?

Heidi: I see it like a Venn diagram because you want to hit that sweet spot in the middle where both needs are met. Tapping into what's important to each person is key. Understand growth paths and directions that people want to go, whether it’s a technical skill or domain area related to the software they want to grow in. But then the company has different needs and strategic directions. I get really excited when companies share opportunities internally that people can volunteer for that map directly to business goals. Someone can be like, “Wow, I never thought I could do something like that here.” And as a leader, you can help make the match. 

Jonathan: I always tell my team, I expect you to be bettering yourself as a professional, and I would love to support you. I will listen to any proposal that you have and see if I can make that happen. I've also had frank discussions with people about the direction the company is going and is not going. In some cases, that means a person may choose that it's just not the right place for them to stay. Business needs shift - some team members embrace that and some don’t. 

Christopher: The onus of growth is always on the individual. Ultimately your job isn't to make someone grow. Your job is to help them when they need it. Sure, there is an opportunity there to help guide and coach, but it's like when you have kids. You can't make your kids go and be something that they don't want to be. If you have someone who is hungry for it, the best thing you can do to help them grow is to take your own ego out of it. You have to take the philosophy that you're trying to get people to do better than you did, to be better than you are.

What should leaders focus on if they want their team to break their dependency on them and operate more autonomously?

Christopher: The first thing is not being afraid of someone replacing you. If I’m able to take five or six weeks away from the company and nothing burns down, then I think I’ve done my job. The positions I’ve been in, I’m thinking, how do I enable? How do I promote? How do I structure? How do I get people to rise to specific challenges? If you've created an organization where decisions go all the way to you as a leader, everything is going to break down. It doesn't create the opportunity for people to rise to that challenge. Take time away from decision making and put it back on to people who may not be used to taking it. Sometimes you have to force them.

Jonathan: I've often thought that the role of a leader is more about providing context than commanding. If the team doesn't seem to be making the right decisions, the onus is on me as a leader because I didn't give them enough context. The rubber meets the road when the team does something that isn't what I would have done, but it meets all the criteria and gets us where we need to go.

Heidi: It's important for leaders to make it clear that, yes, we want you to make decisions. We trust you. We can disrupt the standard centralized communication patterns that we always fall into. Look at your meetings - there are always two people talking and everybody else is silent. You can break through those structures using different types of facilitation patterns, different techniques for bottom up decision making.

How does team structure play into bottom up leadership and how do you know what organizational moves you should make?

Christopher: One of the things that I've been very conscious of is where you are trying to instill leadership and where you’re trying to promote leadership. Not just someone who has the title of manager, but in every level and in every job title. The structure is very important. If people feel like they’re several levels away from the highest person in the company, that creates this chasm where they feel like their decisions don’t matter. One of the things that I've done in the past is essentially made sure that there weren't too many levels of indirection. Everyone from your junior engineer all the way up to a VP or CTO or CIO feels that they can talk to each other. You have people who are leaders, but not so much a manager, not directly responsible for decision making.

Heidi: I think it's really important to be deliberate about decision making, no matter what structure your team has. Whether it's a top-down decision or if it's one that's different, like seeking input and considering viewpoints before making the decision. There’s another type of decision making that’s by consensus - it’s people influencing each other within a team. It’s helpful to have clarity about the kinds of decisions you’re making within the team. You might ask the team directly, what kind of decisions do you expect to make as a team? And where do you need help?

Jonathan: There's a famous law that was put forward by a computer scientist named Melvin Conway. It’s called Conway's Law and it observes that the structure of the system that an organization builds inevitably will map to the communication structure of the groups that built it. I’ve certainly observed that phenomenon throughout my career, but in the last five years or so it's kind of dawned on me that there is a corollary to that. If you want to build certain types of structures, organize your teams that way. And that will be the inevitable outcome.

What does it mean to put others first as a leader?

Jonathan: I think it means being a nice, kind, thoughtful human being. In a leadershIp capacity, I have an opportunity to do both more harm and more good. Speaking of Covid and remote work, people have enjoyed working from home because they've had more chances to interact with family members. But for us right now in our journey as a company, we’re really heads down and we're aggressive towards some goals that we've got to make happen. I’m just slammed, and I know my teams are feeling the same way. How can we make this as comfortable as possible? Can we buy people some chairs or extra monitors? Can we have little gatherings where we sit six feet apart and at least get to see each other face to face from time to time? Little things like that.

Heidi: I think it's also about listening, just being connected with people through various formats, whether it's one on one, in small groups, or different groups that foster uncommon interactions between the teams. And I think it's also about knowing that people have very different realities right now, different situations and different challenges. Stepping in with a bit more compassion is par for the course and a good thing to do, knowing that our situations aren’t all equal.

Christopher: Everyone’s dealing with so much angst and anxiety. A big part of your job is making sure people are OK. As a leader, your job isn't just to deliver, isn't just to make sure that we're hitting our goals, it’s to make sure that people are fine, that they can do their job and that they feel like they’re supported.

Heidi, Christopher and Jonathan had more to say about team structures, valuable resources and general thoughts on leadership in our full Q&A, which you can listen to here.