Category: Technology Leadership

Critical thinking skills are vital in any leadership role, but when you’re leading the technology arm of a business it takes on even greater importance – both for the key decisions you need to make and for the technical people you need to lead.

A CTO needs to be able to reason, understand and solve problems.

Critical thinking is the ability to evaluate the truth of an argument and its premises by subjecting them to rational analysis.

Skills such as logic, analytical reasoning, and problem solving cannot be underestimated in today’s world which is characterised by complexity and ambiguity.

In a world full of information and data, technology leaders and CTOs need to rely on their critical thinking skills more than ever.

This is because they are often asked to make decisions without enough knowledge or data that would help them make an informed decision.

So here are 10 steps for a CTO to improve their critical thinking capabilities;

1. Have an Open Mind and Be Willing To Change Your Beliefs When Necessary

When you have an open mind, it allows you to be flexible and see things from a different perspective.

When you are open minded, then you will be more willing to change your beliefs if necessary.

2. Let Go of Any Judgemental Attitudes & Preferences

Judgemental attitudes are at the root of many frustrations and leadership blockages.

When we judge without understanding, we create separation and disunity. We are all on a journey to enlightenment; it is not our job to judge others for their paths or speed up their journeys.

Don’t judge others because of their choices. The world would be boring if we all liked the same thing. Don’t pigeonhole yourself into one category – this does no good for either party involved.

3. Practice Constructive Listening

Constructive listening is a skill that will come in handy when it comes to solving disputes. It also affects the work environment and helps to create better customer relationships.

Listening is about hearing, understanding, and acting on what is being presented. The best way to do this is by using constructive listening skills. This means being non-judgemental and focusing on what the speaker has to say instead of trying to change their point of view or argue with them.

To start, it is important to avoid interrupting the speaker. If you have a countering opinion or idea, it is best to wait until the speaker has finished their thought before you speak.

Remember that constructive listening involves making eye contact with the person speaking and showing them that they have your attention by nodding and giving them feedback in an appropriate way.

It can be difficult not just for people who don’t know how to listen but also for people who do know how to listen.

Active listeners are not only trying to understand what someone says, they are also trying to figure out why they said what they said and what they think about it as well.

4. Develop Evidence-based Beliefs

Beliefs are often assumed to be ideas that we accept as being true. Beliefs are not always facts though, but rather they are ideas or opinions that we have about a certain topic.

Develop evidence-based beliefs is a process of recognizing the difference between beliefs and facts. There are many pieces of information in our world that we can’t see or feel or taste, but we still hold opinions about those things.

Beliefs are tough to change but it’s important to test our beliefs when presented with new evidence. When we encounter information that challenges a belief, it is important to consider whether there is evidence for the belief being true.

We should never disregard any piece of information as false or invalid simply because the belief doesn’t align with what we want to believe.

There are two types of evidence-based beliefs: empirical and logical. Empirical evidence is derived from sensory experience, while logical evidence is derived from logical argumentation.

5. Evaluate Ideas, Claims, Beliefs, Statements

Evaluating ideas, claims, beliefs, statements can be challenging.

In order to evaluate an idea, a statement, or claim, you need to think about the following:

-Is the idea or claim possible?

-Is the idea or claim reasonable?

-What is the purpose of this statement?

6. Ask Probing Questions

Questions are the bread and butter of any conversation, interview, or meeting. They allow you to learn more about the other person and to explore topics that may be outside your area of expertise.

There are three types of questions that you can ask to get the information you need to complete a project:

Open-ended question: Let your client talk freely about the topic.

Closed-ended question: Ask the person to answer with a yes or no.

Probing question: Ask more detailed questions about specific aspects of the topic.

With this in mind, it is important to ask probing questions that will not only provide answers but also create a dialogue. Questions should be broad enough so that they can generate a conversation, but specific enough so that the other person knows exactly what you are asking about.

7. Think About New Concepts from Different Perspectives

You’ll want to think about new concepts in a variety of different perspectives.

The first perspective is what your idea means for you and your team. What’s the effect for your employees, stakeholders, and anything else that comes to mind? The second perspective is what it means for your company. What does this mean for the products or services you’re providing? Thirdly, shift your perspective to what it means for society, the environment, and anything else with a broad scope.

The last perspective to consider is what it would mean for consumers or users of any product or service that impacts them. Would they be positive or negative about this idea? And how might they react in various situations if this idea were introduced?

This is a great opportunity to get the creative juices flowing.

Think about what you would want to do if you didn’t have any constraints or limitations. What would you do if you weren’t afraid of failure? Imagine that you don’t care what others think or how they’ll react. What would be possible in this case?

As an example, imagine that your company gave you a free pass to go ahead and create something new. You no longer had any restrictions related to deadlines, budgets, or anything else. How might this change your process? Would it change your priorities? Would it change what kind of work you’re doing?

8. Use Data to Support Your Point

As humans we are predisposed to feeling emotions and making decisions based on those emotions. Data is able to make you feel more emotion, which in turn can drive you to a decision.

Data often provides the insight that we need, but it has to be presented in a way that the human brain will comprehend. Numbers and statistics can be difficult for humans to process but if they are presented with the right visualizations, then it becomes much easier.

Visualization is important because when humans see data visually their brains process it faster than if they were just looking at an Excel sheet of numbers. Visualizing your data allows for it to be memorable and shareable as well as simplified for your audience’s consumption.

Data is the best way to prove that something is true or false.

Data can be an effective way of substantiating claims that people make. It can also be used to disprove or dispel myths and misconceptions. Data provides quantitative answers, where other types of evidence may not exist.

People might not trust a claim because it comes from a person they don’t know, but when the same claim is supported by data, it becomes much more persuasive.

9. Avoid Inferring Too Much From the Data

We should not rely on data alone for decision-making but instead apply other sources of information like intuition or expert opinion.

The tendency to infer too much from data is called the “data fallacy.” This fallacy involves two types of errors: “misunderstanding the data” and “assuming that correlation implies causation.”

Data is not a perfect truth and it can mislead us, so we should be careful with the conclusions we draw from it.

10. Know your cognitive biases to avoid them

Be aware of your personal thought patterns through self-analysis, for example, the tendency to selectively remember positive experiences and forget negative ones can lead to disappointment and feelings of hopelessness when things don’t go well.

Incorporate feedback from others through honesty and humility – criticism is a good thing if you’re open-minded enough to consider it objectively and without defensiveness.

Feedback that is too harsh or too critical should be reworded until it’s constructive, but feedback should always be accepted as a gift. It might just be what you need in order to improve your leadership and critical thinking skills.

Build your critical thinking capability with CTO Academy – our online leadership skills courses and coaching can help you enhance your skills in this area.

So here is the scenario …

I’m running as fast as I can alongside my 5 year old son’s bike, initially holding onto his seat to make sure he does not fall.

I’ve made sure we are on a quiet road and there are no cars or obstacles for him to seriously hurt himself. 

Now it’s all about knowing when it’s time, time to let go, time to let him ride off himself.

What I do know is that this setting will allow him to learn in his own way and whilst it’s tough for us to let our kids go out into the world and learn by their mistakes, it’s also the aspect of parenting you accept and almost naturally absorb, despite the reservations   

Strangely I have seen tech leaders (including myself) forget that we have to apply a similar approach to the development of our teams!

“Leadership is not about forcing your will on others. It’s about mastering the art of letting go.”— Phil Jackson

Those of you who have read my previous blogs and/or who I coach, will be familiar with the similarities I draw between leadership and parenting.  

Personally I believe it goes beyond an analogy because the emotions, actions and responsibilities are very similar between that parental/home setting and the leadership/work one. 

What Are Leadership Responsibilities? 

As a leader of teams, we are not only accountable for their output,  but we have a responsibility towards them as individuals.

Effective leaders understand the duality of leadership between helping your organisation and stewardship of the people in the team that they can learn and grow around you and one day leave to further their own career. 

Ineffective leaders look at the short term and often selfish benefits of motivating their team, without pro actively encouraging people to build out their technical skills, develop longer term  soft skills, and create a working environment that encourages a more rounded and structured way of learning, that thinks of the long term benefits for individual as well as the organisation.

For this to happen, we need to ensure we give them the chance to take on new opportunities and the freedom to make mistakes.  

But I think letting go is even more of a challenge for the CTO and tech leaders than most other C-suite roles because we are instinctively problem solvers, lateral thinkers and love getting under the bonnet of a technical challenge. Our instinct is to dive in deep as soon as possible but in a leadership role this is neither a good idea for your own ability to make an impact nor for your team to grow and learn into their roles.

Alongside that natural instinct to get our ‘hands dirty’ we have the pressures of clients, management, deadlines, technical challenges, all demanding rapid answers and results, so it’s perfectly understandable for us to want to just shred all plans to delegate and just dive right in.  

If there are consistent themes to my coaching sessions with tech leaders around the world they are … 

“it was just easier for me to clear down tickets today”, 

“I quickly just wrote the code for the new function x last night as I had some spare time”, 

“I decided to draft the documentation before giving it to the Head of XYZ so that they only needed to finish it off”, 

… different statements, familiar theme? 

It’s easier and faster if I step in and do the work, rather than spend the time to train, teach or let someone else have a go. 

This is such a fundamental leadership mindset that we have to train ourselves to change and it’s sometimes quite a personal challenge having to push back hard on a natural and extremely insistent instinct to just sort it.

But in the words of Elsa (I could not help the Disney reference) … We need to let it go and give our teams the chance to take over, learn and fail and fall, if that is what is needed.  Just like I had to with my son on his bike.

“Are you ready to take the first steps toward leader-leader? Are you ready to take the first steps toward an empowered and engaged workforce? Are you ready to embrace the changes that will unleash the intellectual and creative power of the people you work with? Do you have the stamina for long-term thinking?” ― L. David Marquet

How Do You Learn To Let Go?

To let go, and to let our teams grow, we must first recognise what we are holding on to.  

This can be challenging but if you’re in any form of leadership position then you’re likely to have done some of  this in the past or seen colleagues adopt techniques that help them understand what needs to be kept, or released.

Maybe when you stopped writing production code because you realised your team were just better at it than you,your time better spent looking at the bigger picture of the product.

Or you stopped prioritising tickets and let the Operations team follow the processes that you originally helped create, or it could be you stopped writing user stories and allowed your product managers to have full accountability of the direction of a product?

These are scenarios I’ve seen myself and with my coaching clients, where they’ve realised (not always very quickly) the longer term benefits of delegating certain tasks.

It’s that dawning realisation that a key part of your job as leader is to trust your team and that if you’ve recruited well then they are as qualified and skilled and maybe even more up to date than you to do a particular task. 

There needs to be a realisation also that your pay grade now is such that the other managers and leaders around you are looking for you to add value at a higher, more strategic level in your organisation and remaining down in the technical weeds will not reflect well on your operationally or strategically.

Your job is to inspire and facilitate the team in a servant-leader structure or a leader-leader culture.

How To Build a Leader-Leader Culture

There are many techniques of letting go and letting your team flourish, but a style described in Turn the Ship Around! by David Marquet is the Leader-Leader culture, one of my favourite methods for empowering your team to take ownership and win.  

This technique moves away from detailing exact processes and systems that your team must follow or articulating tasks they must do.  It enables the team to make their own choices and do ‘work’ they decide on.

To deploy this type of culture in your organisation, your role as the leader has to change.  

You need to let go and step away from the day-to-day and your role is to create an environment for your team to thrive and lead in.  You must communicate and empower the team to understand what the overall outcomes need to be and importantly why those outcomes are important to the organisation.

You need to be clear about the context of each situation and challenge, allowing them to come up with the solutions and providing them with the autonomy to execute in the way they best believe it will meet those outcomes.

This technique is hard to execute because as technical leaders we find it difficult to step away from making those hands-on operational and day-today decisions.  

But this is the key learning point as leaders. We have to remove ourselves from some of those micro  decisions being made day-to-day, especially when we see a potential mistake, or a delay due to an inefficiency in a process.  

We must continue to support the team to make the decision and if something goes wrong our role is to support them to learn from the mistake and move forward.

This takes time, willpower (I tell you that from my personal experience) and you will make mistakes and regress to a previous way of working, but your job is to persevere with fostering this environment and over time, your team and the individuals in those teams will perform and deliver more and deliver faster than you could have ever done without this technique.

You will also start to step back as a leader and celebrate the impact you’re having on the organisation, the individuals and your own wellbeing. 

Not letting go is not good for your own mental health and quality of life.

Final thoughts

In every leadership position you will have situations where you don’t have enough time or budget or both to be able to execute on the priorities the business is demanding of you. 

In these situations our natural instinct as technologists and sometimes uncertain leaders is to dive into those weeds and help the team deliver.  

This may help in that immediate moment, it might give you a short term hit of camaraderie and team bonding but what you will lose is the longer term learning culture that fosters innovation and the real leaps in product, quality and team bonding.  

In those moments you must stay strong and remember that your job is to create the environment for your team to become hyper engaged, supportive and productive.  

By creating a safe environment and having the courage to step back, you’re enabling that individual to ride like the wind.

More about the Author

Sanjay Mistry is an experienced CTO and leadership coach with CTO Academy who regularly contributes some wonderfully personal blog articles and also delivers some of our course material, including a recent masterclass on How To Build a Tech Strategy.

More about CTO Academy

CTO Academy provide leadership skills training and career development support to tech leaders around the world. Recently reviewed as one of the leading CTO programs in the world, we focus on helping our customers build the soft skills that really matter to high impact CTOs.