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September 2020
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InIn my previous piece , I observed that leadership is typically recognized rather than anointed. The tl;dr on this is simple: if you are serious about exploring leadership, don’t wait for permission. Instead, look for opportunities to lead now from wherever you are in your organization.

Once you’re starting to do leadership work, it’s important to make sure that the people around you have sufficient visibility into that work. For one thing, this enables your impact to scale. For another: if it’s not seen, it can’t be recognized.

Leadership is recognized, rather than anointed. It’s your responsibility to shine a light on a well-rounded picture of who you are and what you contribute. As an ancillary benefit, this also enables you to take in all the hard work you’ve done and appreciate yourself more, too.

Here’s where to start:

Our protagonist shares their priorities with their leads, peers, and other colleagues

Our protagonist shares their priorities with their leads, peers, and other colleagues

Leadership, whether you’re leading the execution of projects or developing people, entails managing in all directions. In a healthy management relationship, your manager isn’t stalking you or constantly looking over your shoulder.

The tradeoff, of course, is that they won’t see everything. It’s up to you to show them. This is also true for your team. Therefore, intentionally set and regularly communicate your thinking, priorities, changes, and progress. This provides people with the context to work with you effectively.

Invest time to what’s important to your company, your manager, and your team. What are their KPIs or OKRs? Tailor your priorities to reflect them. This ensures that your priorities are impactful and relevant.

Demonstrate self-management

Someone capable of organizing themselves well looks promising as someone capable of organizing others. The inverse is also true: someone who cannot organize themselves looks incapable of organizing others.

Put yourself in the place of a manager with two reports:

Person A comes to their 1o1 with a question: “What should I be working on?”

Person B comes in with a tidy list of no more than 5 items: “This is what I will be working on and why.” Not a granular list, but one that shows where they will be spending their energy and how. Perhaps they also note a conflict of priorities and share how they made the tradeoffs.

  • Who would you trust more as having potential leadership capability? The person who can’t even organize themselves and must rely entirely on you as the manager to set direction? Or the person who already has a vision for what needs to happen? Who would you assume to be most capable at setting direction for others? (Answer: Person B)
  • Note that if you’re truly unclear on what you should be doing, it’s important to highlight this to your manager. Are you thinking about why you are unclear and doing your best to unblock yourself first? Or are you waiting for someone else to do it for you?

You’ll know you’re on top of things when someone can run into you in the hallway and ask you what your priorities are—and unassisted, you can list your stack-ranked top 3–5 top items. This should take no more than 30 seconds to share, much in the vein of an Agile standup. Combine that with you doing those things as planned and updating on what got done, and you‘re looking good—and you’ve made sure people can see it.

Leverage the people around you

Communication ≠ talking at people. It is not read-only. Different people may have additional insight that can help refine or shift your focus—which enables you to leverage your time intelligently. Effective leaders know how to capitalize on the capabilities of their team for optimal outcomes. Using the team to hone your priorities is just one way to do that.

  • DO include things on your mind that you don’t have answers to but are exploring
  • DO include real challenges you’re dealing with
  • DO ask for advice and support. It’s ok to be vulnerable.
  • DO ask if they agree or disagree, and DO actually listen
  • DON’T assume that because someone is more junior that they don’t have insights or ideas to offer you, a senior person
  • DON’T posture like you know everything and everything is fine when it isn’t. The whole point of working with a talented team is to enjoy the benefits of all that talent. The best time to leverage smart people is when there are issues, uncertainties, fires, and you’re running out of ideas.

Every company has “advisors”. These are people you leverage to keep your company on track. At Colingo, when we needed to make important decisions for the business, my co-founder Ben and I didn’t just explore options together—we reached out to our advisors to spar and unpack ideas with us. This helped us get clarity quickly and stay agile in our decision-making.

Similar to a company, you don’t want to be stopped in your progress. You’re measured based on your impact, not on the extent to which you are an island. Consider that anyone around you is a potential advisor, and reach out actively for the right advisor for your present context.

Pretending to know all the answers and that everything is fine is akin to being that balding guy with a bad combover — the only person fooled is the guy doing the combing. DON’T do the career equivalent of a combover.

Our protagonist shares their Year In Review document with everybody

Our protagonist shares their Year In Review document with everybody

Maintain a living list of all projects you’ve worked on to assist with formal review processes and ongoing career conversations with your manager and team.

Being human, we are forgetful

We tend to remember parts of things, rather than the whole. This might mean only recalling recent projects or the details that support the story we’ve constructed about a person or project. Memory itself is unreliable. To offset recency and confirmation bias, the best way to ensure the folks evaluating you have a clear picture of you is to create your “Year in Review”.

Demonstrate your value by quantifying your impact

What is more compelling as a promotion argument?

Person A: “I’ve done good work throughout the year”

Person B: “The projects I’ve delivered this year have netted $30M in revenue, increased customer engagement by 10%, and increased our NPS by 12 points”

If you had to choose between promoting Person A vs. Person B, who has the better argument? If you were choosing a leader who you would entrust to do the right thing for the customer and the company, who would you trust more? (Answer: Person B)

Crispy bullets beat hand-wavy narrative every time, so help yourself out by being extra crispy. This is particularly important if you are a designer reporting to someone who is not a designer, e.g. a PM, CEO, CMO, or Engineering Manager. Make sure you’re framing your narrative in a language that speaks to their values and what matters to the company.

How to write your “Year in Review” (YIR)

I recommend adapting the format to whatever dimensions/values your company uses to evaluate people, and aligning it to whatever language exists for the role/level you’re looking for. Here’s a framework to start with:

  • A paragraph summarizing your accomplishments during the review period
  • Years of industry experience
  • Time in current level
  • A living list of all projects you’ve worked on during that year
    What problem was each project was trying to solve? What was the impact of solving that problem for the user? (the more quantifiable, the better) What was the impact of solving that problem for the business? (again, the more quantifiable, the better) Who worked on that project? What was your role? (from discovery through execution) Include links to project documentation: spec/creative brief, mockups, prototypes, dashboards, etc.
  • Culture development
    How is the team healthier and happier because of you? How do you help foster an environment where diverse voices and experiences are welcome? If so, show it! If not, time to start. Some examples include leading a team offsite, creating a club, and community service.
  • Talent development
    How are you scaling and leveraging your skills to up-level the people around you? On your immediate team, in your org, at the company, and beyond the company? Brown bags, talks, writing, podcasts, workshops, etc. are all great examples.
  • Recruiting impact
    How have you helped the team grow? Highlight interviews, referrals, etc.
  • Values
    How have you embodied company values? For example, if “Be Authentic” is a company value, how have you demonstrated this? What was the impact?
  • Self-development
    How are you actively improving on your strengths and growth areas? Say you got constructive feedback in your last performance review that you need to improve the way you collaborate with PM and engineering. A high performer would have
  • Make sure you also show that you’re actively engaging here so people can envision your trajectory. Highlight any progress made against weak spots from past feedback and areas where you are currently investing. Are you taking workshops? Reading books? Practicing a new skill twice a week? What This can offset confirmation bias based on past weaknesses that you’re already turning around.

When to share the “Year in Review”

  • In review cycles, share it with anyone who is writing a review for you as soon as they’ve consented to write your review (manager + peers). This helps refresh their memory and potentially expose them to new amazing things about you. Let’s be honest — performance reviews tend to be very laborious. The quality of investment in crafting a quality review for a given person can be highly variable depending on how busy or tired the reviewer is. You have an opportunity to up the quality of your reviews by effectively creating talking points that they can easily adapt for their review.
  • With your manager ahead of any negotiation conversation. It’s easier to make an ask when you have something that can help someone remember all the ways they can and should appreciate you. Remember: it’s pretty rare that a manager only has one report, so they’re often juggling a lot in their head. By providing focus for them, you get to sculpt the narrative you want — thus facilitating the conversation you want to have. It can also provide a higher level of detail for a conversation around gaps that your manager might want you to demonstrate more proficiency in in the future.

If you are aiming for promotion

  • Align your YIR to the level you want to be promoted to, way ahead of the promotion cycle.
  • Use this to craft your promotion with your manager, ideally 6–12 months from your next performance review. Where are you already meeting the bar at the next level? Where are your gaps? Together, you can plan out what you need to demonstrate and for a strong promo case.
  • Regularly check in against that plan. Then, come the next cycle, you already know whether you have a viable case for promo.
  • Note that most managers can’t promise that a promo will happen because the decision-making is rarely a solo-enterprise. That said, there shouldn’t be any mystery about whether or not you have a plausible case and whether your manager will back you up.
Our protagonist shares their accomplishments with a bullhorn, creating a stairway to their future career

Our protagonist shares their accomplishments with a bullhorn, creating a stairway to their future career

If a tree falls in a forest and nobody is there…nobody knows about ituntil you tell them. Create visibility, momentum, and appreciation for your team by sharing what your team is working on, why it matters, and what you’re learning and accomplishing along the way. If your team is doing good work, make sure people can see that, making use of any format that feels most appropriate.

Most importantly here, make sure you’re designing the narrative for your audience. Say you want the whole company to understand the project, but not everybody works on it. Write the narrative for the layperson.

Not sure what to say?

Keep it simple and clear

What is the objective of your message? What value are you creating for your audience?

Address the motivations of your audience

Different audiences care about different things. Pass your content through what I call the “Disaffected Teenager Test™”. Answer these questions clearly and compellingly, and you’ll find engagement:

  1. “Sigh…Why does it matter, anyway????” (eyes rolling)
  2. “What’s in it for me?” (arms folded)

Plan for how you want the audience to respond or act

How could learning from you help other people do better work and/or make better decisions? Are you expecting a response? Are you asking for something? Is this just to be informed? Set expectations clearly so people know how to listen to the information and know what to do next.

  • This doesn’t always need to be about being successful.
    Sharing hard-won learnings is super valuable and can model healthy vulnerability to your audience. If a project didn’t go well, but you’re actively learning and sharing why it didn’t, you can help yourself and others make a better decision next time. Obviously, you’ll want to be tactful, but a team that can own its mistakes and actively corrects them is a team with integrity. Compare that with a team that only shares good stories — even when you know not every project was successful (which is true for everybody, no matter how good they are). Which one would you trust more?
  • Consider the altitude of information
    Start with what you want people to walk away with, and edit from there. Edit out details that fail to offer the intended value to the audience.

Share your tools and techniques

Did you, for example, have to create a new design sprint process or product thinking framework to get to a great outcome? How might you teach others that tool? Perhaps you could run a workshop or a brownbag to share it, thus scaling your impact from being a solo smart cookie to creating a more effective team.

Create new forums for exposure

If your team doesn’t naturally have forums for people to share, create a new one. You can start with a small audience of folks you know, build some confidence, and work your way to bigger rooms. Think about how you can create exposure for folks on your team to celebrate their unique contributions.

You don’t have to be on stage for this to reflect well on you, either. Be generous about giving and sharing recognition. We all know that nobody accomplishes something huge all on their own, and we all know how much it hurts to not be acknowledged for your contribution — so don’t do that to other people. Leadership isn’t about you; it’s about who you are for others and how you contribute.

Our protagonist holds hands with people all around them, forming a human chain of strength

Our protagonist holds hands with people all around them, forming a human chain of strength

This is critically important when you are taking on bigger challenges to demonstrate your leadership skills. It’s easy to mistake operating independently for acting like a leader. It comes naturally when you’ve been a star individual contributor and want to prove yourself. However, it doesn’t do anyone any good — least of all, yourself! You want support, visibility, and a tight feedback loop so the folks evaluating you know exactly what to look for — and you know what you need to demonstrate specifically.

Plan your journey

In looking for visibility, you need to sort out what needs to be visible. Where do you want your journey to lead? If you don’t know for sure, which paths seem interesting to explore? How might you develop a plan for testing your appetite for each path?

  • Itemize your leadership goals/questions
  • Then, plan out your development towards them in a timeline with measurable milestones.
  • Share your goals with folks around you so you can refine them together.
  • Particularly for your manager, if they don’t know what you’re after, they won’t know how best to support you. Make sure they’re involved. If you’re not sure where to start, ask: “What do I need to demonstrate in order to move into a leadership role?” And brainstorm together how your upcoming work might fold into that.

Bring people along with you on the journey

Leverage your manager, your peers, and other experts (potentially outside of work) on a regular basis for feedback.

  • Letting your manager into the details of what you’re working on helps them see in higher fidelity how good your work is. Leverage your 1o1s and other forums to show your process, thinking, and execution. You might think it encourages micro-management, but it actually builds trust as you clearly prove yourself and remove outstanding questions.
  • If you are stretching yourself on a project and are trying something new, tell them and enroll them in being a part of helping you be successful. You’re not asking them to solve problems for you, but you’re being vulnerable about not knowing everything and inviting them to assist with their knowledge and skills. This will help build trust with those folks as well through your humility and open communication.
  • Regularly ask for feedback (stop/start/continue is a good starting place) and make strides on that feedback to reward people for investing in you.
  • In doing all of this, you’ll feel a lot less stressed, a lot more supported, and you’ll learn much faster — thus reducing your risk of failure while creating more understanding and patience around any gaps you have.

Close the loop

For people who are investing in you, recapping what you’ve accomplished holistically every so often gives them a return on their investment and provides them with an incentive to keep investing. At the same time, you have some social accountability to stay the course should you have strayed from your plan.


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