What I Learned From Dick Costolo’s Opening Keynote at the PMO Symposium® 2018

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What I Learned From Dick Costolo’s Opening Keynote at the PMO Symposium® 2018

Categories: Leadership

By Quynh Woodward

The performance expectation for a keynote speaker is always high. Keynote speakers set the underlying tone and convey important messages for events. In November 2018, Dick Costolo delivered a spectacular opening at the PMO Symposium held in Washington, D.C., USA.

Dick Costolo at PMO Symposium 2018

Dick Costolo was most recently the chief executive officer of Twitter, serving from October 2010 to June 2015, where he took the company from US$0 to US$1.5 billion in annual revenue. According to Mr. Costolo, there are many paths to success, but to enhance your chances, focus on the speed of execution and leadership.

Here is a breakdown of his tips for strengthening the “speed of execution” muscle of your PMO:

  1. Examine the speed of learning.

On a regular basis at your team meetings, ask the following question: “What is it taking us too long to learn and how can we learn that faster?” This question enables teams to reflect on solutions. The “Why is it taking us too long to learn?” question often surfaces commonly held dogmas or practices that are not always useful or true.

  1. Adopt a bias to yes.

As an organization grows, increasingly the default answer to every question is “no.” The bias to yes means that there are many paths to get to “yes” within the organization to avoid hindering creativity. As long as the activities are legal, encourage employees to innovate and try new things. Avoid the most nefarious version of “no,” which is “you have to go ask these other 12 people for permission.” Your team will spend their time asking for permission rather than taking critical action.

  1. Protect the future not the past (a reference from Ed Catmull).

The job of leaders is not to prevent mistakes, but to correct mistakes quickly. Protecting the or the desire for everything to run smoothly is a false goal—it leads to measuring people by the mistakes they make rather than by their ability to solve problems.

  1. Resist making too many rules.

Rules are set up to simplify life for managers, but they can hinder business results. Instead, replace the critical rules with principles and guidelines, and enable your team to work using their good judgment.

Costolo’s Tried-and-True Leadership Principles

The principles below are based on what Mr. Costolo learned from Bill Campbell, who was the executive coach to Larry Page, Eric Schmidt and Jeff Bezos, as well as Dick Costolo.

Bill Campbell believed that management excellence is about helping people to flourish in their environment, not telling people what to do. Your title makes you a manager. Your team decides if you are a leader.

Principle 1 – Communicate context for decisions rather than authority.

One of the hardest things for leaders is the communication architecture, especially when you are scaling teams. The way to build trust with your team is to listen, be forthright and communicate context for decisions rather than authority. Explain the why and not just the what.

Principle 2 – Push decisions down the stack.

Ask yourself: “What’s the highest-leverage thing I could be doing right now?” When in doubt, force yourself to delegate. Set a weekly goal of the percentage of meetings you will stop attending and start delegating. Make sure action items are delegated to your team appropriately. Give people ownership by providing authority and accountability. As a leader, it is not your job to make every decision. It’s to ensure that decisions get made and to resolve issues when your team cannot reach consensus. If you make all the decisions, then you may become the conduit for organizational politics.

Principle 3 - Eliminate politics.

Avoid being the sole decision maker. A common challenge for new leaders is that they feel obligated to make all decisions. What you may get are pre-meetings before the actual meeting. These pre-meetings are set up to lobby and influence your decision. To eliminate these pre-meetings and politics, you need to encourage debate openly in the meeting room. It’s okay for people to be contentious about a decision. It shows their passion. While social cohesion feels good, getting to the right answer/solution is better. The goal of a manager is not to get to social cohesion, but to get to the right solution. Don’t punish people for debating with you. However, once the debate is done and the decision made, follow Jeff’s Bezos’ advice: “Disagree and commit.” When people cannot agree, don’t get discouraged because contrarians on the team can have great ideas. Send people who do not agree with one another to work together and develop a proposed joint solution.

Principle 4 – Understand the culture.

Ask your teams: “Tell me something that’s not working well.” Get different perspectives. Take notes and don’t agree or disagree with the person on the spot. Reflect to get an overview of the political culture, and learn about what people believe. Take your insights back to your leadership team and act purposely to eliminate political culture.

Mr. Costolo closed out the keynote session with a few of Jeff Bezos’ words of advice:

  • Optimize for debate. When you optimize for compromise rather than the truth, you don’t get the right answer.
  • Don’t let the communication architecture mirror the organizational architecture. Enable people to talk to whomever they need to get the information to do their job. Don’t force them to depend solely on their manager for information.

In one short hour, Mr. Costolo used analogies and simple stories to convey these viewpoints. 

I'd love to hear your thoughts on Dick Costolo's keynote.



Posted by Quynh Woodward on: March 12, 2019 06:29 PM | Permalink

Comments (6)

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Thanks for sharing your notes from the symposium, very interesting and great information ! I like the Bias to Yes strategy !

Leadership always is very important factor for success. But I love the strategy - "speed of execution" .

Excellent post delineating suggestions for success by Dick Costolo.
Thank you Quynh Woodward !!

I like the 1st principle, too often an unexplained decision is questioned.

Would have loved that conference, I wish those conferences be put online later, in a few months.

Thanks for sharing. I like 'Protect the future not the past' - I think this strategy is of utmost importance in today's disruptive world...

Interesting post. Principle #4 is key.

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