As members of the C-Suite, we wear the mantle of leadership in our companies. A mantle is a loose, sleeveless cloak which when you add a light sabre, conjures up images of the Skywalkers. Who doesn’t want to be Luke or Leia Skywalker? Maybe, you already are. Or maybe you are a young Padawan in the order of the Jedi. Either way, you decided to be a leader. And with that leadership comes the responsibility of managing people towards successful outcomes for your business.

One of the most important ways we show up as leaders is with the observer mindset. How do we observe behaviors in our teams and people so that we can bring out the best in them? In the agile software development world, we have a well known practice called Retrospectives. This takes place at the end of a development sprint and creates an opportunity to provide feedback on how the sprint went. Chances are that most participants in the technology development cycle, whether they be software developers, hardware engineers or product managers are well trained in this feedback cycle.

The leader will be forgiven for assuming that with taking up the mantle of leadership, they are already adept at the art of giving feedback. Or by way of career experiences, feel like they already know how to coach their people. But feedback in and of itself has many pitfalls. In the same way, coaching is a widely misunderstood practice that is often confused with consulting. In this article we will deconstruct these skills so that they become powerful tools that affect change and transformation in your organization.

According to the Oxford Dictionary, feedback is defined as “advice, criticism, or information about how good or useful something or someone’s work is”. We have all felt the impacts of feedback. It is quite possible that you took on the mantle of CTO leadership because of a former boss or mentor’s consistent and constructive feedback. It is also possible that you did not continue with another profession or skill due to the negative or hurtful feedback you received from careless comments.

When we provide feedback we give someone an instant and clear picture of what we think about their performance. That picture could be a hot mess. It could also be a wonderful painting of what the future could look like. But in all cases, feedback considers what a person has done and places that in the context of our own experience to formulate an opinion on how to do, or not do the same actions in future.

What is Coaching?

Our world is filled with seasoned professionals calling themselves coaches. Someone builds an e-commerce startup that has a successful liquidity event which leads to the founder giving talks and becoming a coach to aspiring entrepreneurs. Or a Rugby World Cup winning captain becomes a coach to the national side after they retire. These progressions make sense and our psyche is well programmed to understand what coaching looks like.

There is a psychological bias at play in which the sum of our experiences in a field or discipline lead us to believe that we can speak to all aspects of said field or discipline. This bias is known as the Dunning-Kruger effect which simply put, states that we are unaware at how our own incompetence in a field leads us to an over inflated self assessment of our skills. This bias is rampant in the coaching world.

Said bluntly, we think we’re better coaches than we really are.

So let’s take a deeper look at what coaching is and how it can be a transformational leadership skill. The International Coaching Federation defines coaching as “a partnership with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential. The process of coaching often unlocks previously untapped sources of imagination, productivity and leadership.”

The coaching mindset gives the executive leader the opportunity to partner with their people in improving their skills with a focus on the ‘here and now’. It is an engaging process in which we resist the urge to solve problems with one quick chop of the knife. Instead we take time to help our people discover what they see and explore how they want to improve. We are unattached to the outcome. We look for context instead of getting stuck on the content of their challenges.

Who is helping you be a better CTO?

What is Feedback?

Picking up from our collective understanding, let’s take a look at how doing sprint retrospectives trained us on giving and receiving feedback. This form of feedback is a timeboxed meeting that usually takes place after a sprint review. The goal being to provide and process feedback on how the execution of that sprint went. This feedback takes on the form of asking what went well, and what didn’t go so well. The big idea being that we take our learnings into the next sprint in order to hopefully not repeat the same mistakes.

If we take it a step further, as humans, we have been on the receiving end of feedback all our lives. As young children, when we experience certain emotions, we receive feedback from our parents or caregivers. As students, we receive feedback on how we fare academically by receiving report cards. As adults we enter into relationships where we receive feedback, whether direct, indirect, passively aggressive or lovingly constructive.

The 3 Main Types of Feedback

We will discuss 3 main types of feedback:

  1. Appreciation as providing feedback that focuses on the recent accomplishments of an employee.
  2. Evaluation as providing feedback on how an employee is tracking against agreed upon goals and milestones.
  3. Coaching as a form of feedback that partners with an employee on their own aspirations for growth through the job ladder or their career.

Feedback can take on many forms, but in all cases it should be understood that there is well meaning intention behind it. It is a wonderful mechanism to restate the rules of the game and to show our people how to win at the game. As CTOs our goal is to improve performance through having our people feel a stronger sense of self and what better way than to have them feel like they’re winning!

An important general awareness for the CTO is to know that they are wearing the mantle of leadership and just like the whole universe recognizes the Jedi when they show up in their shades of brown, the CTO also is recognized as the final authority. This means that our words carry extraordinary weight and we should make extra effort when providing feedback.

In any organization, hierarchy or executive status could stand in the way of constructive conversations. People don’t naturally relate to each other on status. Command style leadership doesn’t care much about how our people feel about us but we live in an age where we ignore how our people feel at our own peril.

This is why the origin of all feedback lies in our intentions for the relationship we want to create with our people. Do we want to have trust? Do we want to create transparency? Do we have safety to clean up messy interactions? Understand that all interactions happen within the relationship you have, or want to create with your people. This includes feedback.


Consider that we want to give Alice feedback on her most recent interactions with Bob. As two of your leaders, she was openly critical of Bob’s appearance during a recent zoom meeting. Straightforward feedback could look like calling her into a private conversation to make her aware of her actions and to inform her that this will not be tolerated in future team meetings. Hopefully Alice takes this in and everyone continues with their Tuesday.

While this form of communication is well within your purview as CTO, there is a good chance that your feedback has a short lived impact. The impact of your feedback is directly proportional to the trust that exists within your relationship. Trust gets built through appreciation. It speaks loudly and clearly to a person’s sense of value they bring to the organization. And let’s not beat around the bush, it gives anyone who receives it, the warm fuzzies.

To ensure that you enter a feedback conversation with a healthy mindset, take a minute before your meeting to reflect on the good work Alice has delivered to your organization. How has her work made you look good to your peers? What specific work has she done recently that exceeded your expectations? Find a reason to show appreciation.

Appreciation is a cornerstone of relationships because we get to acknowledge each other. It is a universal force between humans that when we feel seen by each other, we will do almost anything for each other. This includes hearing each other out with open hearts. When we have an intention to appreciate, we also show up with a more curious mindset. This allows us to consider the many reasons why Alice may have been careless with her comments towards Bob.

Are you alone in your quest to be a better CTO?


A regular topic of discussion at 7CTOs is on how to deliver effective performance reviews. It seems to be the source of general discomfort for CTOs and I believe it has nothing to do with the personality or style of the person occupying the role of CTO. It lies in our general discomfort with judging people’s performance. This could be due to ambiguity around goals, misunderstandings on expectations or a feeling of not knowing how to develop our people. If there’s one thing that drives us into our holes, it is the imposter syndrome especially when our people look to us for growth.

What if the evaluation of someone’s performance is based on a conversation where you restate the rules of the game and have your person tell you how they performed? You get to reflect back, with courage, on how they showed up as a player and how their work measured up to the agreements that were made. Once again, at the heart of this feedback is a relationship where you can be trusted.

The advantage that both parties have during an evaluation is that they bring different perspectives on the business to the conversation. If this can be seen as a strength then the partnership will be collaborative and flexible to deal with the changes and demands that come from executing on business objectives. The CTO will have insights from the C-Suite to bring to the conversation and the direct report will have information from their team to illuminate possible aspects of the feedback. For example, the VP of Engineering may have a better handle on the overall sentiment of the engineers than the CTO and so if the VPE is being evaluated on slow delivery, the VPE could contribute to the conversation in a constructive way.


By far the style of feedback that requires a shift in mindset, is the feedback that intends to coach the employee to better performance. This is also the most misunderstood form of feedback. To the naive leader, this may seem like a process of telling the employee what to do in order to achieve better results, or to meet regularly with them to measure outcomes together. Under this guise, more damage is done to professional relationships that could lead to employees “quitting their boss”.

The challenge here is that a well intentioned journey could be embarked upon with great energy and gusto but then become a lackluster effort to keep up with meetings due to the stresses at work. Mix this in with leading questions that one might ask a child who isn’t getting what you’re trying to put down or trying to convince your employee based on your own experiences, this could be a disaster.

Personally I love the type of feedback where in response to an evaluation conversation, both parties agree that further coaching is desired, or necessary. Of course, as a leader, having the ability to coach your people is a massive leveling up and I would want for all leaders to have this skill. Here are my ground rules for taking on this form of feedback:

  • Do you have your own coach? Not only does this set an excellent example for your employee, it will guide you towards your own continued transformation. Trust me, your employees will be very happy about this.
  • Do you have the time and energy for partnering with your employee? The beauty of coaching is that we embrace the unknown of what “success” looks like. Instead we allow the growing partnership to produce the outcomes for our employees. This is of course also terrifying for engineering types because we live in a world of discrete values and states that are either true or false.
  • Are you unattached to outcomes? The truth is that if you are truly invested in the success of your employee, you need to admit that they know better than you what is best for them. This may not match your preconceived notions and therefore, if you remain unattached to outcomes, you are able to show up fully for your employee.

When to Use Coaching vs. Feedback

The short answer is that feedback dips into short term memory to make adjustments going forward. Like a pinball machine, the flippers of feedback keep the ball in play. If however it becomes clear that a paradigm shift is required to unlock new potential, coaching is the way to go. It would be like moving away from the pinball game to play something completely different.

The safer your person feels in their relationship with you, the easier it will be for them to receive direction from you. And if that looks like botched feedback or lackluster coaching, the mechanism needs to exist for doing clean up.

Feedback is a great way to keep the car running and on track. Keep the cycles short and keep the content laser focused. Coaching is the way to go if you’re getting out of the car onto the tarmac and into the private jet. But my question is, do you have the courage to create that possibility for yourself?

We help CTOs become world class leaders through Peer Groups and Coaching.