GAUTAM GUPTA

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Simplifying leadership as a CEO

With great humility, I have been trying to boil down the most complicated components of being CEO into the most simple concepts. The functional aspects of raising money, hiring, and managing the board, require a significant part of a CEO’s time and mindshare. It can feel like there is little left to lead the company and as a result, CEOs must simplify their focus. I believe that if there are only three things you can do well as the company’s leader, the three most important are around communication, transparency, and goal setting.

Communication:

  • Develop an operating system that works well for you - lay out a structure for internal communication that you can consistently / religiously follow. You’ll evolve this as the company grows but getting into a rhythm will help tremendously.

  • Over communicate - I remember my surprise in learning how much repetition matters while building a company. Even if you feel like you have said something a dozen times, it may just be registering for many on your team so keep going. Determine your key messages and repeat them at every opportunity (all hands, company wide emails, etc).

  • Develop a culture deck or internal playbook that reviews the company mission, vision, values, and strategy. This can be used in new hire onboarding as a way of level setting new team members but you can also weave key slides into your operating system to drive repetition.

  • Align your communication up and down by sharing the same themes with all audiences. Ideally everyone from a board member to the newest employee are completely aligned and understand the company’s key priorities

  • Let your team figure out the “how” but be explicit about the “why” - empower your team to determine their own action plans but be crystal clear about why a certain goal or initiative is important to the company. Over time, this will not only yield better results but often enable richer understanding of the levers within the business.

Transparency

  • Share as much as you can openly - the more employees know, the better equipped they are in their own day-to-day jobs. Embrace the discomfort. If your business is running low on cash, share the cash balance. Your employees are wondering about it anyway and by sharing the data, you control the narrative. I admire companies who are able to share even compensation data. Candidly, we never got to that level of transparency but aspired to share everything but compensation.

  • If and when possible, share close door discussions like management team meetings and board meetings. The nature of closed door discussions naturally incite curiosity. We formed a habit of sharing management team meeting notes with the entire company and walking through a redacted board deck in our all hands (we redacted option approvals, speculative financing information like inbound M&A interest, and key people performance discussions).

Goal setting

  • Develop a system for goal setting that works for your company. It doesn’t matter if you use OKRs, OGSM, or any other system - the main thing is to have a system that works for your team. Share the goals with the company so that everyone can see what they own and the responsibility taken on by others.

  • The hardest thing about goal setting is to ensure focus on the right things. In other words, keep the main thing the main thing. Rather than being the CEO who is always chasing more (I am guilty of this), be the CEO who is maniacally focused. Less is more in most startup environments.

  • Make sure that every goal can be tied to one directly responsible individual and push goals as far down in the organization as possible. It is critically important to have one person own a goal to avoid any confusion and ensure total accountability / ownership. If the name of one of your executives is on too many goals it can be a sign that either 1) they haven’t hired a capable team or 2) their team is not empowered to be owners. Look for this when finalizing your goals!

  • Scoring - perhaps the most important part of goal setting is to score each goal after the quarter. Whether you are an ambitious organization who chooses stretch goals or a more realistic organization who never wants to miss a goal, the important thing is to evaluate how you did in plain sight. Team members who consistently outperform deserve the recognition. By scoring goals in the shared document, team members who consistently underperform can’t hide either. Scoring goals is a key component to an objective performance management system.

Doing these three things well is easier said than done. However, doing just these three things well could have an immense impact on the performance of your organization and the happiness of your team. If I can do anything to help, please reach out (gautam at m13.co).