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Leading with Context Helps Everybody Level Up

Sharing the vision

1 June, 2021

Stefan Khan-Kernahan, Senior Engineering Manager at Beanworks, shares his experience learning how to open himself up to his team in order to earn the trust necessary for high-level performance across a cross-functional team.


I sort of built my own framework when it comes to leading with context. I also had the guidance of a senior-level architect who taught me the importance of letting my employees in on my vision as a leader. I used to employ a style of management where I was reluctant to let my team know what was really going on in my head, which led to disaster on more than one occasion.

Some managers tell their people: “Don’t come to me with problems. Come to me with solutions.” This approach only works if the people that you’re managing know everything that’s going up, so to speak. Otherwise, they waste time going down a path when you have information that they do not have access to. What is the right way to compel people to take on more responsibility for the work that we all share without misleading them?

One of the things that I was afraid of when first employing this approach was worrying about looking like a fool. Being vulnerable and open is difficult for many leaders. It is a challenge to overcome for the sake of the team.

Actions taken

For me, leading with context in a cross-functional role means knowing everything about the project that I am managing, from marketing to development and everything in between. I filter out the noise and put the relevant information down on paper, describing what we as a team wish to achieve with the endeavor. This is the why. This is the impact that I share with my reports.

As I found myself trusting my team with more and more, it became much easier to manage them because they understood everything in my mind. After giving feedback and seeing what did and did not end up landing properly, now, a year and a half later, I now have seven or eight people who sort of own everything under me, who I can actively talk with about solutions, conversations made possible by the fact that they are in tune with everything that I have going on in my own head.

Over-communicating is not a word that I use; if you think you’ve done just enough, you likely have not done nearly enough at all. This is not to say that you have to let them know every bad idea that comes to mind. This discretion taught me how to have conversations in a variety of areas, providing context with purpose and direction.

I’m a very in-person type of manager, so COVID hit me really hard. Thanks to this approach, however, I never really lost touch with my team because we were already so close in this way. Other members of the team took notice of this newfound sense of ownership and followed suit. Momentum was built and I grew confident in the people that I was delegating these responsibilities to. This also freed much of my time to focus on hiring and other processes that needed my attention.

A year and a half later, everybody on that team got promoted at least once, including myself.

Lessons learned

  • Working in this way relies on trust. You need to get your people to a point where they’re able to just jump in and do some of these things on their own. Provide context, communicate as much as possible, learn how to read people, build a whole bunch of human skills. Then, you can start pushing people forward and leading by way of motivation. You want to inspire people instead of mandating rules.
  • Knowing when to give my own internal context and when to give outward feedback benefited my team and our relationships more than anything else. We gained velocity because people understood the whole ecosystem. I don’t worry about my people because everybody already knows how to operate successfully with one another. Nobody feels like it’s top-down, where I’m holding all of the power.
  • The other side of the coin is earning the trust of your people so that they let you in on where they wish to go, as well. I’ve had reports who have been with me for years before letting me know where their real aspirations were. Part of building this bridge involves actively asking them important questions about where they feel their aptitudes are.
  • A great piece of advice that I’ve gotten: when you are asking for peoples’ feedback, you need to learn to suppress your gut reaction, no matter what they say. You thank them for sharing their thoughts and then you think about it on your own. This is how you mold yourself into a leader. You need to make yourself 100% available to this type of feedback and any questions about what it is that you’re trying to do. Explanations are not motivating for people. This will take some effort from you mentally at first. Leading with context is not just a process. It’s a mental commitment.
  • One thing that I try to tell people: listen to your superiors when they tell you that you are capable of more.

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