How to Recognise the Five Common Mistakes Engineering Managers Make

What does a manager do?

“Organisations are living systems, being composed not just of capital goods and technology, but of people. […] Differently adaptive challenges can only be addressed through changes in people’s priorities, beliefs, habits and loyalties.”

The Cynefin Framework and the Technical Leadership: How to Handle the Complexity

There are many definitions for what engineering managers do. There is no School of Engineering Management that I know of, so everything I write comes from my own knowledge, experience, and opinions; it might be different from your view of the world of management. 

Before being an engineering manager, I went through a string of ‘unorthodox’ experiences and transitioned from a specialist to a generalist. All of these experiences taught me how to: 

• Identify business problems, 
• Create a vision of how the world will look without that problem, 
• Break a big hairy mission into smaller, achievable chunks, 
• Find, support and motivate the right people to create specific goals and
• Uncover unique ways to solve them in different business units, like engineering and operations. 

You can read more about these learnings here, but the most important lesson is that I’m a very fast learner.

I made mistakes along the way and still make plenty simply because I’m human. I like to think that I have enough self-awareness to recognise some of them and lots of courage to ask for feedback to help me see my blind spots.

Some recent conversations have motivated me to share my top mistakes in the hope that both fellow and future managers will read and feel that they’re not struggling alone through this learning process.

1. Not delegating enough

A CTO role in a small startup is very similar to a technical lead. It’s hands-on, at least in the beginning. You start being the manager of one (yourself), then find smarter people who can do specialised things. Your role then becomes about motivating and inspiring them to deliver and even exceed business objectives and expectations. As you make this transition, you start to experience two very uncomfortable things. 

First, you feel you’re losing control of the work. You think there can’t be anyone more motivated than yourself to do the best work. When you see things slipping, you overreact and try to correct them yourself. 

Second, as you delegate more, you feel you’re becoming less valuable and perhaps even a burden to your team – because now they do what you used to. You fear the team might resent you for assigning work to them and holding them accountable for results. You feel the distance and loneliness that comes from becoming their leader and manager, not just their teammate. You also worry about how other founders or executives will value your indirect contribution. 

These are normal first-time manager fears. They can be overcome by reframing your mindset and understanding what a manager does; the goal is to obtain results from a team of highly engaged, skilled and accountable people. If you value these attributes in yourself, then you need to learn how to transfer them to your team. Keep in mind, however, that no matter how hardworking and energetic a leader or manager you are, you can’t make a team great, but you can surely help them increase the likelihood. 

2. Not asking for enough help, soon enough

In early-stage startups, it’s common to have technical leads with line management because that’s the usual way to become an engineering manager: you’re recognised as an outstanding individual contributor and promoted when the team grows. Startups rarely offer support and managerial training to their first-timers. 

You might find it difficult initially to transfer your strong individual performance to your entire team. You could be locked in a continual battle with your Impostor Syndrome or live in fear of being demoted. You may see yourself in servitude to the upper executives, instead of in a collaborative relationship. These notions in your head make it very uncomfortable to reach out for help from other managers and executives. Part of the problem is your mindset and part is the lack of skills and experience. Managers must have a strong combination of intelligence (IQ) and emotional intelligence (EQ). In fact, EQ accounts for 90% of the difference between a star manager and an average one.  Experienced executives in your company already know that great managers deliver by changing the organisational climate, which contributes to approx. one-third of the financial results of a company. They also know that if they could increase the number of talented managers and engaged employees they would get 150% higher earnings per share than competitors. 

The good news is that mindsets can be changed and experience can be acquired through practice. Being fearless doesn’t mean not feeling fear. It’s about being strong enough to accept and overcome it. And being resilient doesn’t mean not making mistakes. Mistakes, bugs, and conflict are life as usual. It’s about learning the lessons and iterating with a new state of mind. It’s also about being honest with what you’re holding yourself accountable to solve and what you need to hold others accountable for helping you succeed.

If you are lucky to be in an environment that cares about building its managers, you will find mentors and coaches that support you through these fears and questions. They won’t have all the answers and sometimes will offer conflicting opinions, but you’ll learn to cherry-pick and apply it to your own unique style and circumstances. You can also reach out to various online communities like CTO Craft, among others.

3. Not projecting enough confidence

Most managerial work happens through conversations, evaluations, negotiations, and presentations. In a remote context, your linguistic style, strength and clarity of your communication can make the difference between an engaged team and an aimless, perpetually confused one.

If you’re a woman, you may struggle more with not appearing confident enough. That’s because your default communication style has been strongly shaped by the societal norms of your country/culture, by your education and by your past experiences. We naturally downplay our certainties in order to invite collaboration and feedback and we also like to share credit more than men do. As I’ve learned, this behaviour can bite you.

Confidence grows naturally from success. It’s also good to leave a healthy margin of intellectual humility so that you’re able to always learn more. If you’re lucky to be in a good environment, you’ll get more confidence by seeing that others acknowledge and empathise with your challenges.

You can also fabricate a bit of luck for yourself by practicing persuasion and negotiation. You’ll have to persuade your team that the work you’re collaboratively doing is meaningful, impactful and rewarding, even if you don’t know that for sure. It’s an unusual mindset change, especially coming from software engineering, where you’re comfortable with shorter, clearer feedback loops: the code either works or it doesn’t (mostly). Human beings are way more puzzling and inconsistent. 

The Effectuation Theory calls this mindset The Lemonade Principle: mistakes and surprises are inevitable and can be used to look for new opportunities. Becoming good at fast experimentation and maintaining focus for you and your team is far more effective than expecting to find the right solution the first time. However, try to balance that with being both effectual (“do things”) and strategic (“but choose wisely what to do”). Otherwise, you’ll end up being Agile In Wonderland:

When things don’t go according to plan (and they mostly won’t), try to be energetic but not frantic. Motivate people into action, especially in critical circumstances or at the start of a new initiative full of uncertainties, but don’t despair if results don’t show overnight.

Also, remember that senior managers and leaders are flawed human beings too. They probably got where they are because they made the same mistakes as you and were fast on their feet and lucky enough to deal with them, learn and survive. If they’re great managers, they’ll reach out to you early on and provide feedback and recognition, since that’s the simplest way to increase someone’s confidence.

4. Not giving and asking for enough targeted feedback

As a first-time manager, you may have butterflies in your stomach every time you deliver strong constructive criticism and discuss performance-related problems with your reports. It might feel worse than if you were to receive this feedback yourself because you’re in a perceived position of power. You might be tempted to rebalance the situation by avoiding confrontation. It might feel more comfortable for you at that moment, but it’s worse for your team in the long run.

You can rebalance that power by delivering the feedback with candour and kindness. My top managerial motto is Kindness Begets Greatness. What this means is that if you want a high-performing team, you should start by treating them as such. Humans are built to respond to reciprocity and we have an inherent sense of responsibility. By starting with trust, you get trust. By showing you’re confident in their ability to execute, they become self-confident too. The team will soon start paying it forward. This is how you transfer your values and your performance to an entire team.  

To be a strong leader and manager, you really shouldn’t be a bull in a china shop. The coercive managerial style is a thing of the past. We’ve long moved away from Specify and Control performance management to Sense and Respond, based on openness, transparency, two-way accountability, self-sustaining and resilient teams. That is the only way to scale tech companies, aka complex human and software systems: by creating resilient, self-organising hierarchies.

As you get more experienced, you start to recognise that good feedback is a gift, a phrase I’ve shamelessly stolen from my previous CTO. 

5. Not focusing on the bigger picture

The silent killer of any managerial career and the absolute hardest to grasp is not letting yourself get caught in perpetual fire-fighting and small tasks.  You also need some idle time to innovate.

The thing I find most appealing about management is the high-level, strategic thinking and building relationships, not about being a technical expert, nor an efficient and organised project manager. Doing all of these is frequently necessary and you can do them by asking good questions, inspiring good habits and leading by example.

You have to let go of the perfectionist tendencies that made you an outstanding individual contributor and your fear of losing control in the situations described above: delegation, asking for help and feedback and projecting confidence in uncertainty. In other words, you need to give away your Legos.

To become a truly effective leader and manager, you have to accept and embrace that listening, communicating, making relationships, mentoring and empowering others is the job, and you need to love it to be exceptionally good at it.

Whiles the five mistakes mentioned above are common, the good news is that there are solutions for all of them. Most, I’ve found, consist of a renewed mindset, plus resilience to discomfort and the courage to experiment. However, there’s no such thing as one solution fits-all in management or strategy. If you’re a manager, you need to find your own way to overcome these challenges, by combining your unique personality, values, knowledge and practice. 

As always, I’m happy to hear more from all of you who have been through similar journeys, so feel free to share your experiences in comments or on social media.

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