The Three Pillars of Coaching All Leaders Need to Scale Their Organizations

Katy Trost is one of The Org's Expert Contributors. She is a leading coach to tech CEOs and Founders, at Series A stage and beyond. She specializes in effective leadership skills, and implementing systems for scaling organizations.

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Based on thousands of coaching sessions with CEOs of tech companies ranging from Series A to Series D, I’ve identified nine areas in three main pillars that have become the foundation of my work as a founder advisor.

Over the course of a coaching engagement, which lasts anywhere between 6 to 24 months, my clients learn to become more effective leaders, implement a system to make their organizations’ scaling consistent and optimize their people and culture. Over time, depending on the growth stage of the business, each area has to be re-addressed and optimized to support the business according to its size and maturity.

To build a startup that lasts, founders must dedicate themselves to becoming the leader their company needs and be open to receiving advice and guidance from people with the right expertise and their best interest in mind.

If you’re a CEO currently scaling a tech company, use the three pillars of CEO coaching — executive coaching, business advisory and people and culture — to successfully scale your company. I’ve combined several leadership methodologies with the Scaling Up framework, a series of one-page tools which more than 70,000 organizations globally have used to successfully scale — many to $10 million, $100 million, $1 billion and beyond. There is no specific order to tackle these areas, simply focus on the currently most painful 20% — nothing else matters during a period when time is your biggest asset. While applying the tools and best practices, make sure you work through them involving the relevant people on your team.

Executive coaching for CEOs

Leadership development

As a company scales, leaders have to grow and develop themselves to keep up with the needs of the business and its employees. First-time CEOs without much previous scaling experience especially must evolve their role and transition from a founder to CEO mentality. Their focus must shift from building a great product to building a thriving, sustainable company. Besides other growth pains such as scaling people and operations, the personal and leadership development of the founder is an important component of long-term business success. The most likely cause of failure after initial startup challenges are overcome is the transition to a functionally organized and professionally managed company.

1. Building a strong executive presence: Confident and charismatic leaders who engage people and possess a motivating presence are critical to building strong relationships with the team, investors, customers and the public. A measured, straightforward and emotionally intelligent CEO instills confidence and has the potential to change the way people work together, improving the culture within an organization.
2. Practicing conscious leadership: Conscious leaders experience what is here now and respond in the moment. They are not trapped in old patterns. They are free to lead and serve others, their organization and themselves. They lead with power instead of force, inspiring their people to fully engage instead of motivating them through fear.
3. Advancing management skills: Leading a team of leaders while helping them enable their teams to contribute to their fullest potential is different than simply managing a group of individuals. Effective meetings, strong performance and behavioral accountability, and a culture of feedback and recognition are only the foundation of great management.

Performance

Scaling a business requires full focus and attention. Most CEOs dedicate 5 to 10 years to building their company, prioritizing their work above all else. Long nights and weekends are part of the mission, which is simultaneously a sprint and a marathon. Maintaining high energy and avoiding burnout at all costs is crucial to sustaining long-term performance and avoiding getting replaced.

1. Improving emotional intelligence and decision-making skills: When someone has high emotional intelligence, they recognize and understand their emotions, can control them and express feelings adequately. Having the ability to see things for what they are and take a step back when necessary, they are less likely to get caught up in their emotions. Decisions are made from a place of calm and clarity, and they respond intentionally to situations as opposed to reacting out of default or habit.
2. Increasing productivity while maintaining a healthy work-life balance: Focusing on one’s strengths and delegating everything that drains energy often starts with the co-founder relationship. As the leadership team expands, CEOs must review their responsibilities frequently and refocus on their zone of genius. With the remaining tasks on their plate, such as setting the strategy, aligning the executive team, building a strong culture, fundraising and building strategic partnerships, calendar boxing is a solution to ensure everything important is covered each week. Dividing the calendar into appropriate, color-coded time blocks also helps with maintaining a good work-life balance. Scheduling personal time with family, friends and being active prevents losing oneself on the journey to a big exit.

Career

A CEO's career strategy can elevate the brand of their company and attract investors, talent and customers. A strong public profile and active networking open many doors. Having clarity on one’s long-term vision is invaluable when making strategic decisions.

1. Establishing a personal brand: The CEO’s personal brand should be treated as a separate business with its own strategy and execution plan. Establishing thought leadership in a certain area is easiest done by pre-scheduling weekly calendar blocks dedicated to interviews, panels, podcasts, writing, conferences and advisory.
2. Leveraging networking: Networking with key people in the industry is one of the most underutilized strategies for fundraising and marketing. Most CEOs are solely internally focused, helping their teams execute. Relevant networks like Reforge, On Deck, YPO, EO, VAB and Startup Grind are amazing resources for introductions of any kind. Any problem a company encounters should never be addressed with a “What?” but with a “Who?” question, making a strong professional network the solution to 90% of any challenge or goal. Strategic partnerships help establish credibility and unlock new customers and referrals at no or very little cost. Underestimating the power of networking means leaving tremendous opportunities on the table.
3. Creating a long-term career vision: Building a company to sell doesn’t mean the founder’s career ends after a successful exit. Having a long-term vision for one’s career is a great tool for strategic decision-making and avoiding an identity crisis after leaving the business. The career vision should be in alignment with the personal long-term vision — something that requires self-exploration and awareness.

Business Advisory

Strategy

Quarterly company offsites are a great way to bring the executive team together for strategic thinking and execution planning. A 3-day offsite in September or October, a 1-day strategy day in April or May and half-day realignment sessions in January and July are an effective rhythm to update strategy and priorities.

1. Achieving strategic clarity and alignment: A one-page strategic plan helps to get everyone on the same page. Updating the core strategy and setting 3- to 5-year goals gives everyone the necessary clarity on where the business is headed and what’s important to focus on. The direction and financial targets should be given by the CEO and co-founders with input from the executive team. Establishing annual goals, milestones and issues helps align everyone on priorities. These should be determined by the executive team with input from the CEO and co-founders. The most important outcome is buy-in — which is gained in the process, not the end result.
2. Setting OKRs: After setting annual objectives (5 to 7 main areas to focus on over the coming year), OKRs (objectives and key results) are a great way to plan strategy execution. Attach 3 to 6 key results to each objective then break each annual OKR down into a quarterly company and department OKRs. Department OKRs are a combination of company OKRs (reflected at the highest level) and local OKRs (not relevant to company OKRs or other departments). The process of OKR setting for the year and quarter, takes one full day, followed by project planning and a final sign-off session.
3. Designing organizational structure with clearly defined responsibility scorecards: Many founders believe avoiding hierarchy is the goal, leaving only a few people as the main decision-makers, which hinders information flow and slows down execution. A proper functional org chart provides clarity on reporting lines, where key people sit, and how employees can progress their careers within the organization. At 100 people the executive team is usually fully built out and manages the VP level. Areas of responsibilities with critical numbers (KPIs) for each department and clearly defined scorecards eliminate blurred lines between roles.

Execution

Once the strategy is set and execution for the year and quarter is planned, managers have to ensure the business runs like a well-oiled machine. Constant firefighting and people working overtime are signs of poor execution. When leaders become bottlenecks and miscommunication happens frequently, people tend to blame each other for mistakes and teams don’t operate at their best. A leader’s job is to coordinate and provide people with the necessary resources to unblock them and make their life easier.

1. Establishing communication rhythms: Rather than colleagues chasing and interrupting each other to find a time to talk, meetings should be recurring and pre-scheduled. If a team doesn't communicate regularly, it’s difficult for everyone to stay aligned with the company’s priorities and critical numbers when setting their individual objectives. Implementing daily, weekly, monthly and quarterly meetings with individuals, teams, as well as the entire company, may seem like overhead at first, and it is. But without a proper management system that assures consistent communication, a scaling organization will create execution issues and lots of drama as it grows.
2. Standardizing processes: Standardizing and documenting core processes both functionally and cross-functionally keeps the business organized and aligned. A centralized knowledge base including a company wiki and processes, featuring responsible people, eliminates confusion and time spent answering repetitive questions.
3. Tracking KPIs and OKRs with scoreboards: After each department determined its most important KPIs with north star metrics and OKRs for the quarter, scoreboards on spreadsheets or in software like Asana or Monday are the most effective way to track progress. Weekly reviewing keeps leaders accountable for what they set out to do, issues surface regularly and people can unblock each other in a matter of days. Additionally, it makes the CEO's job much easier, keeping on top of things across all departments with a simple rhythm.
4. Improving issue resolution: Keeping an “issues list” for all teams across the organization and becoming masterful at problem-solving, conflict resolution and decision-making is a superpower that can improve productivity and team morale significantly.

Cash

Growth sucks cash, requiring founders to continuously access new funding and make smart financial decisions to fully utilize their runway. Knowing how fast a company can afford to grow and controlling overheads accordingly can save a business from growing broke without even noticing.

1. Leveraging cash flow strategies: Improving the company’s cash conversion cycle and using tools like “The Power of One” (1%), a principle developed by Alan Miltz and the team at MyCashflow Story help provide significant positive (or adverse) impact on a company’s cash flow position and overall profitability.
2. Fundraising: Fundraising never stops. Even with a substantial growth rate, companies run out of money when they need it the most, withSeries B often being the hardest to raise. This means CEOs can never really stop building investor relationships. A fundraising cycle often lasts 3 to 9 months, a long time spent externally facing while the company needs its leader the most. Making fundraising and investor relations part of the CEOs' weekly activities with calendar boxing can decrease the actual fundraising cycle significantly.
3. Improving financial literacy for CXOs: A rapidly scaling company must educate its executives on how their management decisions impact top and bottom lines. Communicating the most important KPIs of the company will also influence big decisions such as hiring rate, product lines and fundraising cycles. Having the CEO and CFO be the only people on the team who deeply understand the finances of the business can be a costly mistake.

People and culture

Executive team

Once the executive team is built out, CEOs have to coordinate, develop and enable their leaders. While CEOs can now be more strategic and focused externally failing to help their leaders execute and become a strong team means departments end up working in silos and are unlikely to tackle the company’s greatest challenges together.

1. Building a cohesive leadership team: When a team can engage in constructive debate on important issues and then commit to decisions and standards, members don’t hesitate to hold one another accountable for outcomes. This results in a highly productive team, one of the few remaining competitive advantages available to any organization. Functional teams make better decisions and accomplish more in less time and with less distraction and frustration. They are more likely to set aside their individual needs and agendas and focus on what is best for the business.
2. Developing CXOs: Just like CEOs must develop themselves, CXOs can improve their contribution by continuously advancing their management and leadership capabilities. Monthly group workshops on various topics and individual executive coaching are great ways to develop leaders in their roles. Especially executives who got promoted internally want to evolve when the business grows at a pace that threatens to get ahead of their managerial experience.
3. Leveraging the CEO and COO partnership: Hiring a COO becomes an objective at the 100-people mark. Do not make the mistake of promoting your head of operations into this role. I’ve seen this many times, resulting in the newly promoted COO leaving shortly after. The COO role requires a completely different set of skills. Bringing in an external, seasoned COO with prior scaling experience can be a game-changer for first-time CEOs. Treated as a business marriage, they should not only complement each other’s skill sets but develop trust and build a strong personal relationship. While other jobs are primarily defined in relation to the work to be done, the COO’s role is defined in relation to the CEO as an individual.

Culture

People are the most complex part of any organization. Interpersonal conflicts and politics are common challenges. Once ingrained, it's difficult to undo unhealthy dynamics or save a toxic culture. One bad apple can spoil the bunch. Not paying attention to people and culture can be a costly mistake.

1. Recruiting and onboarding top talent: Consistently recruiting A-level players who support the company’s growth objectives cannot be left to chance. There is a war for talent, meaning everyone has to play their role in recruiting and effective on-boarding. Topgrading is a great methodology for recruiting at scale, offering best practices and the foundation to design a company’s unique recruiting process. Once hired, a unified employee on-boarding process ensures new hires feel at home and helps them contribute to the company’s mission right off the bat.
2. Improving employee engagement: People join companies, but they leave managers. Good managers don’t demotivate and get the most out of their team. They help employees play to their strengths and make their jobs easier. They give a clear line of sight and authority over the “how,” allowing them freedom to figure things out and apply their own style. Great managers recognize effort and show appreciation , giving constructive feedback in a 3:1 ratio of appreciation to criticism. Hiring fewer people and paying above-market rates, then heavily investing in training and development improves engagement and productivity. One great person can replace three good ones.
3. Implementing performance management: Tying human systems such as recruiting, hiring, performance management, compensation/reward and firing decisions into the core strategy improves productivity significantly. Providing clarity on expectations and backing those up with actions encourages employees to adjust to the pace and culture of the company. Performance management systems such as personal KPI and OKR scoreboards and regular feedback as well as quarterly performance reviews are easy ways to track how well people get on.
4. Using values as a management tool: Values help managers build strong and functional teams of self-starters and create a culture that inspires entrepreneurial thinking, creative problem solving, and continuous learning. Defining core and aspirational values ensure behavioral standards are met and can prevent the company culture from getting lost at scale. They are brought alive through regular storytelling, public recognition, feedback and even bonus structure.

Board

The traditional board model is not designed to help organizations accelerate their strategic path and performance but is mainly focused on the past, analyzing and overseeing initiatives. It’s reporting dynamic leads to CEOs spending endless hours preparing board decks and getting members up to speed without receiving real tangible value.

1. Building a high-impact board: A well-functioning board can be a very powerful weapon and even a key competitive advantage to a scaling organization. Engaged members should play an active role in supporting the CEO and leadership team in achieving their goals faster while ensuring governance aspects are taken care of. Helping them overcome challenges, stay relevant in the marketplace, attract talent and fundraise, the board must leverage its expertise and network proactively. It must be focused on the future and outcomes, coming together regularly in a formal as well as informal setting.
2. Conducting effective meetings and committees: After reviewing the board pack well in advance, the board comes together informally over lunch or dinner to discuss the company’s current achievements and challenges and brainstorm possible solutions. Board meetings can therefore focus on pushing ahead and removing obstacles rather than retrospectively reviewing the quarter. Collectively solving issues as a team as well as advising the CEO on an individual basis, board members must justify their position continuously. Setting objectives and KPIs for members is an easy way to measure their value quarter on quarter.