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Digital Leaders: in the AI era, leaders must be more human

In my journey in the world of startups, between the technological centers of Florianópolis and San Francisco, I see a common challenge for all founders of fast-growing companies, including myself: people management. The startup’s maxim is to grow fast in revenue, win the market, launch solutions that solve real problems, and launch before others do. But the secret of the best startups is to acquire and maintain talent. Good people, good performance, good company. Great people, excellent performance, excellent company. That simple.

But yeah, it’s actually not simple at all.

So the question is: How do you become a leader capable of attracting the best talent? And how do you keep that talent? It is a mixture of two points:

  1. The culture of the company – I will share some learning that I had in my journey with Contentools.
  2. Continuing Leadership Development – There are some very practical structures I learned in Silicon Valley that are able to help with management and I included them in the final part of this article.

Shall we?

Great dream, mission, and values

In the early phases of Contentools, when we still had the first version of our product (our Minimum Viable Product, or MVP), we gathered the team to define our vision, where we wanted to make a change – we created our Big Dream. Now, with products in the global market being used by more than 1,000 marketing teams, we re-did the exercise. We included dynamics in which we visualized the world 20 years from now and how Contentools will be when that date arrives. The result goes well beyond the alignment of the team. It is a true guide that allows us to anticipate the outcome of our journey; the impact we want to bring to the world.

With this, the operations team (which takes care of talent acquisition) is already able to do a first analysis of new candidates to know if they will meet the challenge. This guide also helps our product team prioritize new features. Along with customer requests and market movements, we might ask: “Will this release bring us closer to our Big Dream?” If the answer is yes, it can be prioritized. If the answer is no, we will not invest resources in the development.

The mission is important. By registering it we can identify why we are together on this journey and know that all the effort will be worth it. It creates a horizon point for us to aim for. Therefore, it is essential that this definition exercise is jointly determined by a large group that collects data from all departments and represents the entire company. It is a tool that generates purpose and commitment in the day to day.

Another fundamental tool is the recognition of embodying the cultural values that make up the company’s character and people. What do we all have in common? How do we see the world? How do we act? Do we want to attract people who think and act in what way? The answers to these questions shape the organizational behavior and actions, having a profound impact on the organizational climate. In the case of Contentools, our values are the cut-off line of any selection process. The items assessed in the evaluations have a significant impact on promotions and layoffs, as I will explain in the Ritual of Recognition section.

Management Rituals for Digital Leaders

We perform weekly, monthly and quarterly practices that give rhythm to the company’s management. The main ones are our Rituals of Alignment, Recognition, and Development. I will delve a little bit into each of them:

Fim de Ano Contentools

Team gathering to close the year and have fun

1. Ritual of Alignment

This is the ritual of creating and resetting goals for each year and quarter. At Contentools, we use the OKRs (Objectives and Key-Results) methodology for this. This methodology started at Intel and became better known when it was deployed by Google. At the time, the technology giant had only 20 people.

We started using OKRs when the Contentools team had 15 people. One of the challenges was to follow the goals on a day-to-day perspective. But overcoming this challenge from the outset was indispensable. After all, there is little point in setting great goals if you only measure each one of them when the quarter is ending. To ensure that these goals are achieved and to correct the route on time, it is necessary to follow-up carefully. Team leaders need to play a key role in this monitoring: they help team members in their weekly challenges to achieve quarterly goals.

To this day, Google uses OKRs to establish and track goal compliance. At Contentools, each quarter the team meets to establish the goals for that period and follow-up on the results. These goals are scaled within each team of the company and all team members create their personal OKRs to contribute to their respective teams. This makes everyone clear about their impact on business growth.

2. Ritual of Recognition

At Contentools, each member of the team is evaluated according to the following criteria:

1. Delivery: how much of the established OKRs the person actually fulfills;
2. Potential: whether personal advancement is aligned with the company’s goals and how much of the 360 feedbacks the person puts into practice and uses to evolve;
3. Cultural fit: how much of the company values the person puts into practice in their daily tasks.

At the end of the assessment, the team leader answers: “Would I hire this person for my team, today?”. If they say “yes” and the performance of that person is way above average, this team member can receive recognition, in the form of a bonus, promotion, honor and/or prize. If the answer is no, they’ll receive direct feedback and deadline for the expected improvement. If the improvement does not match what’s expected, this individual may not be right for the role and is potentially asked to leave. Thus, they have the chance to find a place in a company in which they can grow and contribute more, and we are able to maximize the potential of someone who is more suited to our team and that role.

3. Development Ritual

The Development Ritual is when we set a time for structured exchange of suggestions among people from the same team, and between teams, using a form for suggestions from people from other teams as well. With this ritual, we encourage more moments of feedback to occur on a daily basis.

At Contentools, each team goes through the ritual every three months and everyone is encouraged to give feedback to everyone. The main structure used is “When you do this… I feel that…“. This was a framework we learned from workshops with experts from a Silicon Valley leadership and a founder training organization, called Inner Space. It’s a model that encourages us to share what we feel and think from the attitudes of others — a field of vision that is commonly confined to ourselves. By broadening this field, seeing our attitudes from the vision of the team members who work side by side with us, we learn a lot about the expectations we generate and ways we can move forward for the benefit of the whole team.

Digital leaders are in continuous development

Whether you’re a leader in a digital or offline company, you’ll need to recruit and retain talent from a new generation. A generation that needs to continually feel engaged, challenged and constantly learning. Some tools that are in vogue in Silicon Valley can help you make this task easy — namely the FlowGraph and Radical Candor.


This structure of keeping the team in an optimal flow of productivity and engagement is proposed by Cynthia Maxwell, who was the Engineering Director at Yahoo!, Apple and most recently Slack. She applied this self-assessment methodology to software engineers. At Contentools, I tested with people from the business teams and it also worked very well. The idea is that the depth of the challenge the person has before them versus the skills they have to perform such challenges must be in balance.

To put this idea into practice, you can create a simple graph, where the X-axis represents their Skills and the Y-axis represents the Challenge. Then ask a team member to grade from 1 to 10 to the Challenge before them to deliver the expected outcome of the quarter. After that, ask them to grade from 1 to 10 how prepared they feel to deliver on their challenge (in terms of training, information and technical training).



Enter the crossing of these numbers as a point on the chart and notice where the point is. The target area is within the Flow Area. Very large challenges and low skills result in the ‘Doubt’ or even ‘Anxiety’ areas. A lot of skill and low challenge results in the areas of ‘Nostalgia’ or, in more serious cases, ‘Boredom’. If both are low, it is a risk of ‘Apathy’; poison for productivity.


The idea of ‘radical candor’ comes from a framework proposed by consultant Kim Scott, who led Sales and Operations teams at companies such as YouTube and Google, and launched the bestselling book titled Radical Candor. According to Kim, feedback routines need to be heartfelt. But what is the limit of honesty? It is the extent to which the leader really cares for the person they are leading to the point of challenging them directly.

That is, if you challenge someone on your team directly so that he or she improves, you should really care. That’s what Radical Candor is all about. After all, just challenging others without caring will make you an aggressive leader. In the other quadrants are the leaders who do not present challenges. These are the manipulators, who do not care, and the disastrous empathists, who care, but still do not present a challenge.

So in your next feedback session with the team remember to offer suggestions that actually challenge a person to become a better professional, but really do take to consider their success and their life (not just the immediate result).

The thing is…

To found a startup or work in a startup one must be emotionally strong. Delivering far above market results month after month and year after year puts any leadership structure in check. I hope this information helps your day to day development of high-performance teams!

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This post has 2 Comments

  1. Congrats for the article and the history that you and Contentools are building.

    Cadence is key to build a high-performance team, and all the rituals that you guys are doing led to that. As well the feedbacks during the year.

    Tks for sharing.

    1. Thank you, Cesar. Even though we see the importance and impact of such practices every day, your feedback as a thought leader provides us with the right motivation to keep going!


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