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A letter on fit

I wrote this letter as a cathartic process to identify what wasn’t working in my work life. This method helped process my emotions and bring more confidence to my decision to move on. This letter was written in August 2019.

Cultural Fit

I’m in shock and overwhelmed. I had moments of hyperventilating on the streets of Stockholm. I am full of mixed emotions. Happy, sad, angry, disappointed, and frustrated.

I think I’m about to get an offer of a lifetime for a dream role. Ironically, I’ve already gotten another one. This means there will be two offers on the table within the period of 3 weeks. I also know that every role in my career has been a once-in-a-lifetime opportunity. My talents are rare, and I know I’m privileged.

As I reflect on these two future opportunities, I’m thinking about my current role and scenario. Strange enough, my current position has been the most challenging but relatively junior in my career. Let’s call it growing pains from shifting disciplines. I love the product space, peers, and my teams but am not being supported by leadership. They are intelligent and talented. Their positive intentions come from a place of “knowing.” The challenge is that their “knowing” is limited. They are naive and lack the skills to change.

At least once or twice a week, I’ve been approached by a person who is in tears, and they claim:

  • They feel unsupported, unheard, and bullied.
  • They don’t have enough impact.
  • They are not getting enough direction.
  • They are being micromanaged.

Most of the time, we are told to figure it out and be patient. Thus the imposter syndrome begins because the context is complex. See, we are in a hyper-growth phase of the company, and this is normal. So many people are new, and the folks that “know” are not available. I’ve been at Shopify for over a year, and I have the most context outside of 4 people on this 70 person team. Those who have context have left the company because they are either burned out or are now in senior positions where they cannot spend time with us.

Where are the rewards?

Another challenge is that there are no rewards for slowing down and onboarding people. Therefore, I’m also not rewarded for coaching or onboarding folks. So, if I take this time to invest in people, it takes away from my impact. I am conflicted because, as a seasoned leader, investing in people’s growth is part of my skillset and in my values. Should I continue to support these conversations? YES.   

We are also a group of people who often give aggressive non-concrete feedback. Such as; You aren’t delivering! You are spinning too long. You aren’t making progress fast enough. You need to become a domain expert. Remember, we aren’t rewarded for onboarding, so it becomes this vicious cycle. Unfortunately, people have not been trained to listen to feedback, or feedback is given top-down. There is an opportunity to coach individuals and teams on how to receive feedback at all levels!!!

I see many resilient people. They want to make it work. They are eager to figure out how to make it work. They need feedback that is concrete and leaders working with them to see their success. That means there needs to be time for leaders to coach and translate their profound knowledge to others. I believe this needs to be solved by changing the way we reward and level folks. We need to look beyond just paying for impact and look for how they collaborate and transition knowledge. I saw this change at Microsoft once they made a 33% reward from what you impact directly through your craft, 33% from how you delivered your impact, and 33% on how you help others impact. That last 33% means you will make the time.

Why could I not get enough coaching or support?

But let’s get back to the concept of support. What could that look like? Instead of saying “that’s wrong”, “that’s not how”, or “we don’t do that here”. Why not build on the ideas? Work together and extend a person’s vision. I don’t see this practiced. We work towards one idea and provide a result. However, if it’s not what the senior leader wants or was in their minds, you go back to the beginning, and teams continue a cycle of stabbing in the dark. There are ways to solve this. A leader could simply tell us what to do if they already know. Plus, I’d be happy to do that for some time, especially at the beginning. However, a preferable way would be to allow the person to try it out. Be willing to let the idea be another approach.

This isn’t accepted. This also means I cannot share drafts or stages of the effort. It must be clear and precise. There were times, I spent days perfecting a few words in a project brief. Did that really matter? As a creative and an external processor, this creates a space I can not perform well. I love collaboration, where we build connections and redirect each other on ideas.

I see these challenges are not discipline-specific or level-specific. It’s apparent in every group across the company as I coach those who come to me with tears or frustrations. I have to swallow my own emotions and be present. I have to “lie” and be positive. I’ll help remove the negative emotions and gain a sense of positive motivation out of the person. All my coaching skills have come to light.

I have a question: How can a company with excellent cultural values with high achievers have such a toxic environment for me? It boggles my mind because not a single person I’ve met is malicious. Everyone comes from a good place with great intentions.

So, I found myself coming to terms with that I’m just not a good cultural fit for my current employer. Did I try? Yes, I saw a coach every two weeks. I read books. I sought help across the company. I came up with many ideas and tried them week after week. I talked to leads and my lead. I tried their advice. I second-guessed myself, and I lost my confidence. I didn’t like the person I was becoming. I also found I spent more time working on these things than the actual work. I was simply not heard. At some point, I felt I could not impact change in the product, process, or team. I was not hired at the level to impact these changes. I had tried. I gave up. I’ve never given up on a role in my career. 

Why could I not make this work?

So this brings me back to the choices I have to make: two incredible roles, both once-in-a-lifetime opportunities. I’ll be leaving the culture of this company even though it was what made it the most appealing when I joined. I’ll be departing feeling I have failed.

Recap of challenges and solutions to consider from above:

  • Consider how you reward individuals in companies. Rewards should reflect your values and also reflect the state of your company.
  • Consider a 33% – direct impact by craft, 33% soft skills on how you had an effect, and 33% on how you help others deliver their impact.
  • As a hyper-growth company, we need to retain context and reward people with knowledge sharing and onboarding. 
  • Provide coaching to individuals new to leadership, such as giving and receiving feedback, coaching versus commanding, emotional intelligence, self-awareness, coaching on humble inquiry, and precision questioning.
  • Also, provide training in Clifton strengths, tilt365, or similar. They help leaders establish their own strengths and weaknesses. This can help a leader be more effective with teams not only by craft but also by strengths. 
  • Reward leaders for being great leaders (unblocking others etc.)
  • Create an environment of failing fast or accepting of failures. (There is a practice of micromanaging here from dictating delivery to process)
  • Calibrate changes and expectations often (At least quarterly, be in the NOW)
  • Don’t be so hard on yourself.

Additional observations to consider:

  • Company values are not the same as your own values. Be wary of the company’s values on paper because they may not be the same as your future leader’s values. Company values can be compelling, but each person interprets and practices company values from their own perspective. There can be a mismatch of interpretation between people within one company or your own interpretation. When exploring roles, have more profound conversions on how each other’s values translated in their experiences.
  • Inexperienced leaders will see more weaknesses than strengths. They can not identify ways to shift variables to ensure a person’s success can be achieved. Therefore over-indexing on a person’s faults and projecting their own methods as the preferred method of excellence. They also could not utilize individuals where their strengths can be maximized. A different team, a different role, or another project can lead to significant results. 
  • This particular company focused on individual achievement, not team orchestration. Therefore a hero was celebrated. Not a team. In my experience, I’ve done my best work in diverse teams working together towards a common goal. 
  • Inexperienced leaders have a perception bias, and that bias may be hard to change. Once biased, their influence can spread to others preventing a fresh start. This can also be true with experienced leaders. Sometimes you can make a mistake, and there is no way to come back from it. Therefore, it’s sometimes best to find a new opportunity where your skills are best utilized.
  • Spend time with the teams or conduct skip levels to get a sense of team challenges (what’s broken in the process on the individual level)

Update: I didn’t get the executive role in Stockholm, but I was close. Two days later, I got another ping for an executive role in London, but that role didn’t feel right either. I resigned from my position at Shopify in October 2019 and began my new role as Head of Design for Agile and Dev Ops at Atlassian in November 2019 in Sydney, Australia. This has proved to be the best decision I could have made.

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