Coaching: One of the best investments you can make


Asking for help is not a novel practice. Neither is wanting to be better than we are. But personal development is now part of the workplace since the explosion of startups, globalization and remote working Millennials and the Gen Zs, who actively seek meaning and development through their work, are increasing in the workforce. And you guessed it, It’s the workplace that employees first look at to help them develop their potential. It’s also the workplace that business leaders look to apply their leadership skills.

But as we all know, chipping away at yourself is not easy. Self-improvement goes hand-in-hand with feedback; that’s when working with a coach can be helpful. Coaches help to move you towards action and create a structure tailored to you. They are meant to provide honest feedback and should act as a sounding board.

Coaching in the startup environment.

It goes without saying that startups have less structure. It is common to find employees who consistently have to do more as the startup environment is designed to encourage employees to go beyond. But as the startup grows and more people join, the hierarchical structure of the startup starts to emerge. Building trust into the culture becomes crucial for the startup’s survival. One of the key aspects of building trust is creating psychological safety in teams. Another element is coaching.

Founders first
Coaching in a startup is a multi-layered, cascading process that starts with the top. Founders typically seek coaching to be better leaders. Coaching is almost necessary for the survival of the startup. “Founders have a huge task of shouldering the vision of the company, every single day, regardless of the ups and downs, and more so when times are down. They often find themselves lonely in this journey but still need to muster the energy and resilience to be persistently creative and effective.” points out Goh Yiping, startup coach and partner, Quest Ventures.

“What coaching does is to provide a sounding board with no agenda in mind except for the founder’s agenda. It offers an outlet of mental release, to explore different perspectives and instill clarity. Since the coach only holds the founder’s agenda, this opens up deep genuine conversations that are not commonly discussed elsewhere.”

Founders have a huge task of shouldering the vision of the company, every single day, regardless of the ups and downs, and more so when times are down.
— Goh Yi Ping (Startup coach and partner, Quest Ventures)

Instilling a coaching culture

As founders develop into stronger leaders, it is expected that employees start feeling the impact of strong leadership. Typically, the impact is first felt by the executive team, then company leaders, senior employees and will start spreading to all employees. Typically, founders, CEOs and leaders become de-facto coaches in the company due to their seniority and experience. However, in a startup, it is common to find founders and leaders younger than their employees - is coaching realistic in this scenario?

Goh Yi Ping (Startup coach and Partner, Quest Ventures). Photo Credit:

Goh Yi Ping (Startup coach and Partner, Quest Ventures). Photo Credit:

Yiping weighs in, “Coaching can be done by anyone of any age. But I recommend taking proper coaching courses before representing yourself as a coach. Engaging external coaches to coach both the founder and senior employees is a good alternative. It’s also important that both employees and founder(s) align with the company vision first work, and then work towards its execution.” 

Coaching for employees should happen with their managers. Periodically, external coaching sessions are helpful to provide perspective. A range of personal development tools, such as Emergenetics, are available to provide custom feedback. Coaching sessions need to be distinguished from other 1-on-1 sessions. Coaching sessions should focus on improving performance, problem-solving or long-term goals. They should have goals, an actionable plan and must focus on empowering the employee to do more because he is capable of doing so. Investing in coaching for employees early benefits the company as performance issues can be managed earlier. 

Asking coaching questions are about provoking reflection and thought. Vague questions related to work are a big no-no, as they are too general and instead create more questions. This should not be confused with asking simple questions. Drawing from the book, The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever by Michael Bungay Stanier, this article points towards 7 simple questions, asked in sequence, which are used to set context for reflection.

A quick note: Mentoring vs Coaching

Mentors and coaches are not alternatives to each other. They have different functions and often complement each others’ roles. Unlike coaches, mentors are not paid and do not operate on a fixed schedule. Mentors provide guidance on the bigger picture and strategy. Their advice is rooted in their own experience, insights, and knowledge and their focus is on overall development rather than specific skills or actions.

Coaches, on the other hand, also provide guidance but do so by asking questions. These questions are designed to force reflection. They guide you to draw your own conclusions and figure out the roadblocks that are preventing you from reaching your goals. Coaches are about the nitty-gritty; their focus is on specific actions and improving certain skills.

Tip Sheet
Many people tend to be skeptical of coaching and this is why: it’s easy for coaching to fail. Coaching is an intensely personal experience and requires genuineness and honesty from both parties to be successful. It’s important to select someone who you feel comfortable with, be willing to be vulnerable with and whose judgment you trust

In conclusion, Yiping suggests the following to incorporate coaching for startups:

  • Engage coaches that have gone through proper training

  • Coach leaders first and then review the outcome of coaching on the leaders. The impact of these coached leaders will cascade down to a better work environment, better relationships. 

  • Keep a safe environment where coaching conversations remain confidential and non-judgemental to breed trust and honesty.

  • Coaching cannot be approached as a one-off exercise. Frequency of coaching matters and it usually takes about a minimum 6 sessions to work through most situations


Coaching Perspective: The struggles of startup employees

Twelve rules for effective employee coaching

How to coach teammates: A key responsibility of effective leaders

Five times a career coach is well worth the splurge

TED: Atul Gawande - Want to get great at something? Get a coach