Newsletter #122 : Lead with Intention

March 22, 2022





Welcome to what is the 122nd but last edition of The 5 Minute Tech Break!

But this is not the end, only the end of the beginning as from next week we will be shifting gears and providing you with two very focused newsletters per week …

Monday Mindset – a look at the individual self and a focus on how to become a more effective leader

Friday Finds – a look at the digital world and a curated perspective on what you should be aware of as a technology leader

Thanks for all your support these 123 editions
Much more to follow …

Andrew Weaver
Co-Founder, CTO Academy

In this 5 Minute Tech Break, you’ll find out:
✍️ How to lead with intention
?‍♀️ Why you should change from top-down  to team-centric
? The importance of knowing your TAM


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3 steps toward being a more intentional leader
Leadership by Alfred Aloushy

Humans are great at adapting to change.
But sometimes to adapt, we turn on the autopilot. 

This might be acceptable in mundane roles but according to Shawn Casemore, if you want to achieve the goals of a corporate strategy, you have to stop putting out fires and making quick decisions – but you have to lead with intention. 

Here’s Shawn Casemore’s 3-step strategy outlined: 

1️⃣ Be clear about what matters to you

You have to clearly write down the goals you want to achieve related to high-level stuff like corporate strategy and key results and learning/development plans for individual employees. 

The secret sauce is: to sustain your intent to achieve these goals, make sure you understand why you want to be intentional about it anyways. 

What will these goals actually give you? 
And are they aligned with your objectives?

All in all, you can say “I want to” as much as you want but if you don’t find the underlying purpose, you will only get mediocre results. 

2️⃣ Set an intention so purposefully that you must commit

Casemore mentions that when he started his coaching business he wanted to: 

“build a company where [he]  could assist clients worldwide and earn enough to support [his] family.”

But only later he discovered his purpose was to help clients achieve higher results.

Now, with his family on the line, he had to commit to his purpose. 

Should you put yourself in painful situations to over-perform? Of course not. But you should put your self-respect so high that achieving your purpose is a must. 

3️⃣ Document your progress, good and bad

Studies show that writing down your intentions is crucial to your success. Next step: review them weekly and score yourself. 


Collaborative leadership: 
Moving from top-down to team-centric – [Part 1]

Photo by Cherrydeck on Unsplash

We read this great article from Slack on how one-third of millennials say that in 10 years, the CEO role won’t be relevant in its current format.

“The new generation of leaders is flattening vertical structures and organizing like ants to enhance collaboration, agility, and collective intelligence.”

Collaborative leadership has clear benefits …..
Employees being more engaged
Team feeling trusted 
People are more likely to take ownership

So how do we prepare for moving towards collaborative leadership?

1️⃣ Clarify your common purpose
Instead of rearranging your teams based on skills or specific pipelines, clarify your common purpose and rearrange your team to achieve that purpose. 

“[The Cleveland Clinic] focused on improving relationships by recognizing all employees—and not just physicians—as caregivers. This stood in contrast to hospitals, where the primary relationship is considered to be between the doctor and the patient.”

The new model resulted in increased quality, efficiency, and positive patient experiences.

2️⃣  Keep communication lines open
Often as techies, we feel that there are many topics the other departments don’t understand. However, we need to know that the struggle is worth it. 

Based on Pixar’s experience, it is worth the investment of time to train staff in specific skills they need to know just so they can openly communicate with the whole organisation. 

Is your product an automation software? Train the paid socials department in the basics of RPA. Over time, it’ll be worth it.  

3️⃣ Build partnership skills
To build a good partnership you need to be ready to accept that everybody’s experience will be different. 

Even though you believe someone might have learned something you believe to be incorrect, all experiences are still valid. 

So if you’re the boss, you can’t use your power to make your team member’s experience undiscussable, wrong, or uncomfortable to bring up. Or else they will find the door. Fast. 

Working through conflicts is crucial. It’s something we go into detail about in the CTOA Academy Courses. Check here how you can join us. 

4️⃣ Don’t waste time
The hardest thing about collaboration is that it is complex and messy. From my perspective, it’s way easier to clean up a google sheet than collaborate. 

The challenge is: implementing leadership techniques to the whole team without having to overhaul and change the whole organizational structure. 

The solution: Give yourself time to think of all the ways you can implement the different collaborative leadership techniques. There are hundreds of ways. 

The hack: make sure the techniques follow your current workflows. 

5️⃣ Don’t be afraid to show vulnerability
Just because you are smart, doesn’t mean you should be the one having all the answers. 

The core of collaborating with your team is actually saying “I don’t have the answer – help me”. 

Including other people’s perspectives in developing solutions will always bring better solutions. Very often, they are a good use of time – not a waste.

What is waste, however, is letting your ego run loose. You have to accept that your idea might not be the best. 

Stay tuned for Part 2 coming next week
(or click here to read the full article)


The demystification of Total Addressable Market (TAM)

Photo by AbsolutVision on Unsplash

Huge part of creating a viable value proposition particularly when it comes to raising investment is estimating market size, competition, growth, size of investment, and the realistic market size … not the overall global market, but the market you can realistically aim to attack.

That’s where TAM comes in. 

The Total Addressable Market is defined as the overall revenue opportunity that is available to a product or service if 100% market share was achieved. 

The TAM is extremely useful as it can help startups prioritize specific products, customer segments, and business opportunities. 

There are 3 main ways of estimating TAM but we like the article’s example of the Top-Down approach: 

Imagine a company offering an app for startups that cannot afford premium accounting software. The company knows that there are 1 billion relevant businesses and 30% of them lack access to premium accounting software. That’s 300,000,000 potential customers. 

Then, 90% of businesses without a premium accounting application have a full-time accountant. Potential customers = 30,000,000

If the business is offering the application for free but with subscriptions of $100 per year, the estimated total addressable market is $3 billion (30,000,000 x 100). 

Find out more about TAM here




Four Thousand Weeks
By: Oliver Burkeman

Four Thousand Weeks – Oliver Burkeman

Drawing on the insights of both ancient and contemporary philosophers, psychologists, and spiritual teachers, Oliver Burkeman delivers an entertaining, humorous, practical, and ultimately profound guide to time and time management. 

“Most of us seek a specifically individualistic kind of mastery over time.

Our culture’s ideal is that you alone should control your schedule, doing whatever you prefer, whenever you want—because it’s scary to confront the truth that almost everything worth doing, from marriage and parenting to business or politics, depends on cooperating with others, and therefore on exposing yourself to the emotional uncertainties of relationships.”


? This week’s wins of our community

In our online community for global tech leaders, there’s often a lot to celebrate. 

Here are highlights from this week:
We always love to celebrate good news for members of our community, particularly when they have some game-changing announcements.

Stjepan Buljat, the CTO of Cognism, and his team have kicked off 2022 securing an $87.5 million investment … Now that’s what I call a good start to the year!

Santiago Garcia da Rosa is CTO at Nowports who has just been recognized as one of Y Combinator’s Top Companies … not surprising given their amazing growth with recent Series A and B funding rounds.

Down in Sydney and all change for Ben Caldwell and his team …. 
As “Practice Ignition” rebranded to “Ignition”, reflecting their growth from being a core proposal and payment automation solution to a broader client engagement platform.



? Latest from The Digital MBA


Our 2nd cohort (the Turing Cohort for those who are interested) set sail this week which means we currently have 51 global tech leaders taking part in this exciting course.

Feedback about the lectures has so far been fantastic with an average lecture rating of 4.7 out of 5 plus we’ve received some really useful comments about the user experience, helping us to constantly iterate and improve.

The next cohort launches on Monday 28th March with a 20% discount available to anyone on our database, who signs up before 14th March.

Find out more information about The Digital MBA for Technology Leaders and/or contact [email protected]


Did you know:
If you sign up for CTO Academy, you get:


? 340+ Lectures on Leadership
? Access to our global slack community
?‍? Access to Live Group Sessions
? Regular Expert Webinars
… and much more

Learn More


This Newsletter was written by Jeppe Strands and Andrew Weaver


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