Agenda 2023: Life of a Start-up CEO?

Not just young companies, today, start-ups have a life and identity all of their own. In 2022, there were nearly 80,000 start-ups in India, up from just 471 in 2016. Of this, 14,000 new start-ups were given recognition in 2022, and 20 entered the unicorn club.

That is why the role of a start-up CEO is becoming increasingly more common and remains just as demanding. They are both decision-makers steering the ship and on-ground soldiers shaping a company’s culture, conversations, and employee engagement. A glimpse of what a day in the life of a start-up CEO is an excellent way to understand the DNA of this unique new phenomenon of the last decade. And, it may have some lessons for you as well. Most CEOs of Start-up’s excitement levels are high. Thus, they are excited about the new day, and their sleep memories are full of ideas.

Morning (Problem Prioritisation Phase with self):

Excitement and engagement drive the morning wake-up pattern of the CEO. Of course, different people start their days at other times, but in my experience, a typical start-up CEO will wake up sometime between 5 am and 8 am. It ensures adequate rest, essential for one’s mental well-being in a high-pressure role, and enough time for independent and focused work.

The day’s first task is thinking about ideas/problems they slept over, and the second is planning — i.e., self-project management to understand the previous day’s backlogs, tasks involving other stakeholders, and long-term priorities. Thinking is a parallel task in the background; alongside this, most start-up CEOs will make room for a light breakfast, a coffee, and a quick workout. A well-structured morning routine prioritising self-care and personal obligations before the day starts is recommended, but excitement takes over. Thus, they ignore the formalisation of the day or adherence to the schedule. Instead, most start-up CEOs will rely on a simple project management or task management tool in the mornings to reduce the cognitive burden and leave room for the big ideas.

Late Morning (Problem Prioritisation Phase with the team):

While a start-up CEO’s job is seldom 9-to-5, it helps to have a repeatable routine. It assures team members that the person is reliable and predictable and reduces the burden of deciding how to spend time on routine tasks, like getting from one place to another. Therefore, the late Morning work is best performed in a designated workplace, a conference room, a home office, a coffee shop, a partner/vendor site, or a traditional cubicle. Hence, the idea for the CEOs to call this part of the day should be the “Problem Prioritisation Phase” of the day so that backlogs, background ideas and benefit maximisation can bind the team. The leader must focus on physical inspection (lead this personally and not delegate) of the broken technology, process, experience and commitments. The way to do it would be to call for a hands-on meeting for 30–45 min to document actionable viz the Objectives Key Results (OKR) plan, so that process/people who have entangled the progression can be aligned or gaps can be closed. Post the prioritisation build-up activity, and the CEO should keep an open-door policy to ensure availability to address gaps with teams & respond to personal communications/tasks.

During this time, which lasts between 9 am and 1 pm, the start-up CEO remains accessible to others and available for impromptu conversations. It is often crucial to transparency and openness and aiding various ideation and brainstorming processes through the cognitive diversity in the contributions of others.

The Problem Prioritisation Phase need to be supported by a framework of quick decision-making with minimal information. It will be necessary for readers to study The Consequence Model developed by Kristian Kreiner and Soren Christensen. It states that knowledge grows over a time period or any event or problem. However, the decision impact reduces as well. We cannot get the timing right, but we must make or defer decisions and take responsibility for the consequences.

Afternoon (Design Deficiency Deliberations Phase with self):

During lunch and keep an additional half an hour after lunch for you to gather your thoughts to identify the broken-down systems, processes, people and gaps that need attention to continue the chosen path. It is essential to remove cognitive bias while jotting down your meeting notes, as these influences define the remediation or solution before, we understand the problem. The way to reduce cognitive bias is firstly, not to trust your first impressions, secondly, not to trust or follow anecdotal evidence and lastly, to assume that you can be wrong.

Late afternoon/evening (Design Deficiency Deliberations Phase with team):

Post lunch, i.e., 2–4 pm, almost always combines a meeting or a team event, the start-up CEO touches base with critical stakeholders in the company, including the CTO of a product company or CMO, for the discussion around the brand or customer outreach or COO to address scalability problems. What takes precedence for C-Level depends on the size and nature of the company; they make time to make decisions on the product, sign off on marketing campaigns, update board members and shareholders, troubleshoot product bottlenecks, and sketch out future moonshots. The CEO may also devote a portion of their time to financial analysis.

This last part of the official workday is about complex decision-making and cutting through the clutter. With so many moving parts, every action item may seem like a top priority: nothing is an agenda. That is why a typical startup CEO will take this time — usually between 4 pm and 7 pm to organise their thoughts and discuss the prioritisation task with senior team members.

Before we solve the problem, we will isolate the occurrence of the problem under various categories of mistakes so that the cause-and-effect model adoption can help in promoting the issue. The Swiss Cheese Model by James Reason 1990 helps in categorising mistakes

- Process mistakes: the process chosen is wrong, part execution of the process, process part is forgotten, or an execution error.

- Capability mistakes: Knowledge was inadequate, skills were missing, or rule base understanding was inadequate

- Structure mistakes: technical provisions were short, team formation inadequate, and the supporting environment was not task oriented

Unfortunately, mistakes take time to identify as we deal with symptoms, not the actual cause.

This part of the day, The Hard Choice Model (The Decision Book by Mikael Krogerus and Roman Tschappleler), requires attention, which puts decision-making as a choice between options available and the consequences of the decision. The decision is thus a choice, a trade-off between them. However, aligning and carrying the team is another matter altogether. The decision choices emerging from the matrix are

a) Ease of comparison between the options & one choice, no consequence, so it gravitates to low consequence choice.

b) Difficult to compare, and the consequences impact has to be weighed, so it takes time to analyse the options and do a trade-off. However, collective bias can make decision-making easy, which can be built by having substantial value and ethical culture.

c) Ease of comparison but consequence impact is significant, and these are primarily risk-based decisions where you can only move forward by taking the risk or cost. Not taking a decision is not an option.

d) Complicated options and consequences are heavy, and the challenge lies before the team. The basis of decisions is subjective arguments and role-holder authority rather than logical or rational choice. Such decisions take time and require focus, attention and resolve to make the hard choice.

Non-urgent decisions are off the table for a later time. Still, predetermined date, and the CEO may also look after the operational aspects of running a company at this time. Notably, a start-up CEO’s job is both of a disruptor and maintaining business continuity. Therefore, later afternoons/evenings on operational matters like compliance, payroll, employee engagement, etc., are critical as they develop the organisational foundation.

Late evening (Inform to Innovate with self or team):

A startup CEO’s job can informally extend beyond 7 pm; later, they may take this time for more research or creative pursuits. First, however, a few days a month are required to be set aside to share knowledge, gather knowledge & apply knowledge with young minds, industry or forums. Secondly, it includes spending time with friends and family, learning a new language or skill, social media or brand building, dinner meetings, reviewing pitches, and other cognitively rewarding or challenging tasks. As a start-up CEO, a big part of the job is not to get “stuck in a rut” and to remain open to new, game-changing ideas. Evening activities support and build on creativity and mental health.

Lessons learned

A typical day for a start-up CEO reveals several vital lessons. First, I call solo time think time and teamwork are equally important, which is the collaborative planning & execution time, and one inspires the other. Second, one must minimise systematic or non-value-adding efforts, such as keeping track of reminders to utilise one’s time optimally. Finally, productivity is impossible without focusing on mental health; hours of rest, meals, exercise, community and creative pursuits can balance it.

The CEO work breakdown structuring is around PDI i.e., Pre-Delivery Inspection process performed in automobile industry. Thus, the CEO must perform routine tasks daily, address broken-down systems, processes and performance capacity and innovate or get informed to be ahead of the curve. The PDI steps are

- Problem Prioritisation Phase with self and team

- Design Deficiency Deliberations Phase with self and team

- Inform to Innovate with self or team

Did you find this article interesting? Let me know in the comments below or join the conversation by emailing me at Arvind@am-pmassociates.com.