It’s that time of the year again. Soon, we’ll all rush to announce the new year’s roadmap and goals. Some resolutions might be declared. Unfortunately, it is far too easy to go through this rigmarole on autopilot without actually leveraging it as an opportunity to better ourselves. To help you avoid that mistake, here is a suggested assessment for yourself, your management, and your organization.
Make sure to turn this into actionable decisions. Grab the free worksheet at the bottom of this article.
Tailoring
A quick disclaimer: In my coaching approach, I continuously emphasize the importance of taking into account your particular situation and circumstances. Thus, a generic assessment won’t be complete for everyone. What a CTO should measure in a pre-seed startup will only partially overlap with what a VPE will measure in a more mature startup.
That is to say, if you go through this assessment as-is, you will already be doing better than most tech leaders. However, taking some extra time to adjust it to your scenarios, either yourself or with some help, can greatly increase the efficacy of your assessment.
Personal
This is the first part, as often we are our organization’s barrier to improvement. The leaders who invest in themselves and constantly grow are those who tend to lead better organizations. When it comes to the cause and effect here, I tend to think leaders’ deliberate work is the catalyst.
Traits and skills rating: If you are honest with yourself, this can help shed light on areas you should focus on. It should be as simple as rating yourself between 1-10 (1: you’re the worst in the world at this, 10: you’re the best). Choose traits that make sense personally. Here are some examples I use with my clients: Executive mindset and optimism, effective communication, ability to delegate, accountability, and coaching skills.
Trends: It will be easier once you stick to this assessment and hold it yearly (or quarterly), however, you can probably already tell the “trend.” Regarding the skills you just considered, how many have improved lately? Which are actively becoming a bigger issue? Which are your “stills” (areas where you’ve been stuck for a while now and might need help with)?
Time management: Compared to your ideal week, how much off is your average week? To do this, you should start by having an ideal week in mind and thinking about how best your time should be spent, of course (that’s covered in this video). Where you are spending too much time can be an indication of areas for improvement (e.g., if you’re putting out a lot of fires, perhaps the team needs to improve its quality).
Decision-making: Review the past year and consider the big decisions you’ve made. In retrospect, how well did they pan out? Think about decisions like promotions, hiring, reorgs, bets you’ve placed, and similar. When it worked out, think about why. When you make the wrong call, ensure that you’ve learned from the mistake and extracted the most out of it (so you’ll be making new types of mistakes). Oh, and of course, are there decisions that you’re actively waffling on or that you took too long to make?
Product mastery: How familiar are you with the product, the users, and the business in general? As the year progressed, did you lose touch with the product or actually get to know it better? Leaders cannot be disengaged from the actual product because then their decisions are “vanilla” ones.
Executive Seniority: This is what I usually refer to as “moving upstream.” Are you operating at the right altitude in the company? For example, many VPEs rarely speak up in strategy and roadmap decisions (if they’re even invited to them). They take orders instead of helping shape the plan. They don’t speak “business” and don’t view themselves as peers of the rest of the executive team. What is your current standing, and how has it changed throughout the year?
Feedback: Lastly, feedback is essential to any improvement and retaining our touch with reality. How much feedback have you received? How much of it was the type that’s hard to get but valuable (as opposed to people stroking your ego or telling you what you wanted to hear)? How did you act when you received critical feedback?
Management
Your direct “work” should be about the organization’s health and how it is being managed. Where below we’ll cover the straightforward “velocity” and delivery, management should be about shaping that trend and increasing velocity—acceleration.
Talent growth: If you consider each person in your organization, how many have tangibly grown and improved over the course of the last 12 months? We want to avoid cultures that accept Peter Pans: employees who remain juniors forever and are stuck at a certain level. Seniority is not gained automatically purely with the passage of time.
Hire review: How many hires still make sense? Were there particular types of hires where your process seems to have done worse? For example, I routinely see companies struggling when it comes to hiring managers or very specialized engineering roles. Hires that, in hindsight, you wouldn’t have made should trigger two different tasks. One is to address the issue itself and ensure that either that person rises to the expected bar or is replaced. The second is to improve your hiring process to reduce the odds of the same mistake being made.
Coaching: One of the most important tools in any leader’s toolbox should be the ability to help people grow and become better. That’s directly related to the first question in this section, naturally. Moreover, you should assess the coaching in all ranks of the organization. Your engineering managers should be devoting enough time to investing in their teams.
Clarity and vision: If you were to survey your team, how many would be able to describe the company’s vision and goals? The strategy that is used for the decision-making? For example, do they understand why the roadmap looks like it does and what the priorities are? Unfortunately, many times, such an exercise of asking N different people results in as many different answers.
Management level: Lastly, are you and the managers under you treating management as a bona fide profession? Is the average manager actively working on improving skills like a determined IC would? How many are the equivalent of a junior and yet are in charge of critical projects without getting enough mentoring and attention?
Organization
The last part is about the health of the organization under its responsibility of delivering.
Roadmap delivery: Though for many companies, this is not a trivial feat, I consider this the bare minimum. The team should be reliably delivering what it has committed to do. Drop the excuses.
KPIs: I recommend choosing a couple that are important to you and measuring those. For example, you can rate your team based on quality (e.g., how many issues are reported), cycle time, and uptime. Tracking these is especially useful when they can be utilized to ensure the team is improving across the organization.
Profitability: Profitable engineering is about creating an organization that will fulfill software’s promise of creating businesses where the additional cost of each customer is approaching zero. It is a subject whose scope is bigger than this article, but you can read more here. If things continue like they are going, will the team still be sustainable when the business grows 10x?
Innovation: Another aspect that sets the best engineering organizations apart is their ability to learn how to work smarter as opposed to harder. How much novelty has your team introduced? It could be very tricky to measure, but it can include tracking how many initiatives from R&D turned into viable features, the accumulation of tech capital, and similar.
Process and Overhead: The last point is about the “operating system” that you’re using to run the organization. Without noticing it, we tend to accumulate many recurring events and rituals that no longer make sense. If you don’t deliberately take the time to review how you work, this cruft will bog you down. What should be changed? What are strengths that should be applied in other areas?
Going through this exercise should float many different opportunities for growth and improvement. Let’s make the next year even greater! If you realize you could benefit from investing in yourself, consider my Leadership Leap offering. And if you want to go through this assessment thoroughly, fill out the form below to get an assessment worksheet in your inbox.