Are You Managing Your Manager?

This post originally appeared on FirstMark Community.


Insights from FirstMark’s Code Driven series, a monthly event for developers to learn and get inspired.

Are you doing a good job managing your manager?

Duncan Grazier, ShopKeep’s VP of Engineering, has a simple formula that can empower engineers to get the most out of their managers, and to ultimately take charge of the direction of their careers. In fact, the formula — — shared at FirstMark’sCode Driven NYC — has the potential to unlock personal and professional growth for anyone with professional ambitions.

There is a virtually endless library of business writing dedicated to being a good manager, from classics like High Output Management or The Goal, to newer managerial approaches like radical candor. But this advice does little to empower employees to take charge of their own careers. Grazier’s formula turns professional development on its head: how can employees draw great management out of their managers?

The idea holds enormous promise, whether you’re currently working under a terrible manager or a great one. Drawing from his experience managing engineers, Grazier’s formula consists of four simple steps, succinctly summarized as dreams, alignment, goal-setting, and feedback.

Step 1. Dreams: Know What You Want

“Cat: Where are you going?
Alice: Which way should I go?
Cat: That depends on where you are going.
Alice: I don’t know.
Cat: Then it doesn’t matter which way you go.”
Lewis Carroll, Alice in Wonderland

First, you have to know what success means to you. What are you working toward? Do you want to become a CTO? Start your own company? Or, are you happiest as an individual contributor? Do you want to write a book on software development? Become a widely recognized thought leader? What do you want to be when you grow up?

Countless employees clock in every day without having any long-term career objective. Others may have blind ambition to “advance” their careers, without any specific achievable outcome. Both of these scenarios leave you and your manager unable to make progress, because there is no specific end state you are working toward.

With a specific dream in mind, you can approach every day like it’s one more step on a longer journey. Without direction, you may still “advance” in one sense of the word — but, like Alice, it doesn’t matter which way you go if you don’t know where you’re going.

Step 2. Alignment: Make Sure You and Your Boss Want the Same Things

The next step is to figure out how your dreams align with your manager’s and your company’s priorities.

What’s critical is not simply to know what you want. It’s equally important to know what motivates your manager, as well as your company. Because the success of this formula hinges entirely on figuring out how getting what you want also enables your manager and your company to get what they want.

If your ambition is to become a VP of Engineering or CTO, there are countless ways you can take steps toward this objective while simultaneously supporting the growth of your manager and your company. For example, you can seek out opportunities to mentor new or junior team members, who will benefit substantially from guidance from an experienced hand. This gives you the opportunity to practice doing what managers do (providing mentorship), and prove to others that you are adept at it. It also makes your manager’s other reports more effective (an outcome aligned with her interests) and your entire company stronger.

So, the crux of step two is to have a candid discussion with your manager about how your dreams align with your manager’s and your company’s goal. Make sure she understands what you want to accomplish and how you intend to get there. But do so in a way that emphasizes areas of overlap between your interests and the organization’s. From there, you can work together to figure out what specific areas of focus — the heart of step three — are aligned with the objectives of everystakeholder.

Step 3. Goals: Agree on Specific Objectives to Get from Here to There

Grazier believes goals are the single most important tool you have as an employee to become successful. (He also believes it’s the single most valuable tool in the manager’s toolkit, as well.)

Goals provide a framework that enable you to be extremely deliberate about your day-to-day focus. They help dictate what tasks you focus on, encouraging actions that carry you and your organization toward your shared objectives.

One common symptom of a broken goal-setting process: engineers who feel like their only job is to write heaps upon heaps of code. Without more specific guidance, ambitious engineers can only ramp up output in an effort to stand out. For engineers, writing code is the main focus of your full-time job, but it’s likely not the only part of your job. And it’s almost certainly not the only thing you should be doing to achieve your professional ambitions.

So, if you don’t have them already, demand goals from your manager. With the alignment you’ve established in step two, it should be straightforward to set specific goals that meet everyone’s objectives.

Goal-setting is a topic that has been covered at length in business literature. In short, though, Grazier believes there are just a few simple principles that govern great goals:

  • Goals should be set at both micro and macro levels. Most often, this means setting time-bound goals with different cadences: weekly or monthly objectives (“ship feature X”), paired with broader long-term goals (“four mentorship sessions with three employees over the next year.”).
  • Goals must be measurable. If goals are not quantifiable, whether you’ve met them — or not — becomes a subjective question. Goals should be time-bound, and have an objective and quantifiable binary outcome.
  • Goals should be challenging. The purpose of the goal-setting process is not to “lower the bar and step over it.” Nor is it about setting impossible-to-accomplish targets. It’s about finding a happy medium that is achievable when you stretch to do your best possible work.

For more information about effective goal-setting, you can read up on SMART goals, or any number of other resources.

Step 4. Feedback: Make Sure Your Manager is a Mentor

The final and most important piece of the puzzle is regular feedback. Grazier is adamant that engineers demand it if they aren’t getting it. Feedback could come in the form of a weekly or bi-weekly one-on-one meeting. It could even be an email- or Slack-based check-in. The format isn’t important; what matters is that it happens.

Feedback sessions should include a systematic review of progress against your goals. The check-ins give you the opportunity to be honest with yourself about where you stand within the organization, and whether you’re making steady progress against the goals you’ve set in step three (and, by extension, your ultimate ambitions set in step one).

A candid review of your goals naturally segues into a conversation about ways your manager can help. Are there organizational roadblocks that need to be removed? Do you need resources that you don’t already have? There’s certainly somethingyour manager can be doing to help that she is not doing already. And, because your goals are aligned with your manager’s goals, it will be in everyone’s interest to make sure those things happen.

A final important note about getting the most out of your manager — you have to be willing and ready to learn from your manager. As Grazier says, “They have probably done your role. They have probably been in your shoes. Maybe they have some really interesting insights into what you’re doing. But, look to them as mentors. Don’t look to them as ‘Oh, that’s just my boss. He’ll decide my bonus.’ Sure, that’s true. But they have more experience than you, likely. They have good insights into what you can be doing better.”

Regular and candid feedback is what keeps this entire process on track. It’s your opportunity to assess your progress alongside your manager, identify how to remove roadblocks and move faster, and get the guidance that will take your career to new heights.

Conclusion
Managing your manager is as simple as this four-step process: dreams, alignment, goals, and feedback. Give it a shot; you may be shocked to discover how much you can accomplish if you decide to become a better manager of your manager.

“Begin at the beginning,” the King said, very gravely, “and go on till you come to the end: then stop.”
Lewis Carroll, Alice in Wonderland