How to become a more effective Chief of Staff?

Let's face it, speed and efficiency are alluring. In startups and scale-ups, efficiency metrics and slick operational dashboards feel like progress and control. "Doing more with less" is the mantra chanted in boardrooms from Shoreditch to Silicon Valley.

But are you doing the right things?

Decades ago, Peter Drucker said: “There is nothing so useless as doing efficiently that which should not be done at all”, and this is arguably more important today than ever. In our relentless pursuit of optimisation, are we just efficiently marching down the wrong road? 

Why do we get so hung up on efficiency? It feels good. It feels tangible, measurable, and controllable. In today's volatile and unpredictable world, it makes people feel safe. Here lies the efficiency trap.

• Scaling processes in the service of a flawed go-to-market strategy.

• Acquiring more of the wrong customers and increasing the team to go after the same customers you know will more than likely churn. 

• Celebration of high "productivity" vanity metrics based on outputs (e.g., number of meetings booked, support tickets handled this month, number of QBR’s run this quarter, number of visits to that expensive stand you paid a small fortune for) rather than outcomes (e.g., real revenue growth, profit, market share etc).

• Spending many sprints polishing and perfecting a feature that few customers want or need.

With AI increasingly being implemented across organisations, the risk is that there will be a focus on just speeding things up, leading to more waste, missed opportunities, and your teams' precious time spent integrating AI and optimising for the wrong things. In this era of volatility, accelerated change, and smaller moats, we must remember, “If the ladder is not leaning against the right wall, every step we take just gets us to the wrong place faster. We may be very busy, and we may be very efficient, but we will also be truly effective only when we begin with the end in mind.” R. Stephen Covey. 

Now is the time to reevaluate and question, starting from a foundation of first principles: What is needed and why? What do we need to stop? How can we do this differently to increase the value we create and capture?

Just because you are focused on setting up and integrating AI workflows, are they impactful? Are teams drowning in AI-optimised busywork that is moving you further from where you need to be?

Effectiveness, on the other hand, is the engine of real value. It is about deep insights and making tough decisions. It’s about ensuring the direction is right before you optimise for the speed of travel. 

• Is everyone in the organisation going in the same direction, towards the same clearly defined goals? (Tushman, O’Reilly, and Nadler’s Congruency model can help you with this)

• Is your limited time, money, and talent focused intensely on the few initiatives that will drive disproportionate results? (OKR’s, V2MOM’s, Eisenhower Matrix can help here)

• Are you addressing the core customer need or just treating symptoms? Are you solving a painful problem for a defined market willing to pay? (Look at the KANO model or the Jobs To Be Done JTBD models here)

• Are you building for where the market is going, where it is today, or worse, yesterday? (The RICE model might work for you here)

• Are you brave and pivot from things you have always done?(Start-Stop-Continue Exercise, Identifying the 7 Wastes (Muda - from Lean) could be used)

• Are you experimenting, or are you doing what you always have?

As Steve Jobs once said, "People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas."

Effectiveness requires stepping back, questioning assumptions, and making tough strategic choices. It means saying 'no' to many good ideas, to protect the focus on the freaking great ones. It’s less about the how and more about the what and why. There is a window of opportunity to reevaluate what you should focus on and what you can stop. If not wasted, this window will allow you to accelerate away from others and compound gains.

This requires different actions from each person in the organisation. From a Chief of Staff perspective, you are the critical bridge and often the organisational conscience for effectiveness. Yes, drive operational improvements and efficiency gains, but always ask: "Is this making us more effective at achieving our core strategy?" As Jim Rohn said, "Don't mistake activity for achievement."

Your role includes:

• Ensuring strategic clarity, alignment and commitment across the organisation. 

• Translating vision into effective execution plans, and ensuring there is a feedback loop to learn, iterate and improve what is and what is not working.

• Building systems (planning cadences, metrics dashboards) that prioritise and measure effectiveness (outcomes), not just efficiency (outputs).

• Protecting and supporting your Principal's strategic focus to maximise their impact.

• Having the courage and ability to influence people, initiatives or processes that are efficient but strategically irrelevant or wasteful.

• Support your principal from being influenced by premature optimisation or running in several directions. Ensure you are building the right machine before you fine-tune its engine. Always remember, "The essence of strategy is choosing what not to do." Michael Porter.

Strategy, and thus effectiveness, is defined as much by the paths not taken as by the ones pursued. It’s about making deliberate choices about where to focus effort. 

The goal isn't to abandon efficiency. It's crucial for scaling and profitability, but it must serve effectiveness. Get the strategic "what" right first, then optimise the operational "how." A Minimum Viable Product (MVP) mindset is essential here. Get the core effective solution out, then learn, iterate, remove, simplify, iterate again, and only then should you look to optimise and scale.

In The Art of War, Sun Tzu says, "Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat." He argues that you need both, but implies that having the wrong strategy (ineffectiveness) leads to failure, no matter how well you execute the tactics.

Getting effectiveness right isn’t accidental. It requires consciously building the right environment, habits and mindset in your organisation. Here’s where to focus:

1. Culture & mindset:

• Psychological safety. Create an environment where people feel safe questioning assumptions, flagging ineffective strategies, or admitting they don't know something without fear of retribution. This fuels better communication, smarter decisions, and higher performance.

• Challenge the status quo. Actively question the "this is how we've always done things here" mindset. Encourage proactivity, experimentation, curiosity and a willingness to revisit so-called “sacred cows” if they no longer serve the strategy.

• High performance and impact. Do the best with what you have. No matter what stage a company is at and what resources you have, you need to deploy them in the best way. Most great things come from individuals and organisations stepping outside of their comfort zone and pushing forward. This mindset of an organisation needs to come from the top and be encouraged and rewarded throughout the business.  

2. Protect focus:

• Combat context switching. Identify why and where your teams are constantly switching gears (too many meetings? Slack chaos? Office layout?). Protect deep work time.

• Streamline comms. Cull redundant Slack channels. Eliminate pointless status update meetings that could be an email, short video update or asynchronous post – free up people’s time for deep thinking and impactful work.

• Simplify or remove before automating. Before jumping to automation or optimisation, always look to remove or reduce steps, unnecessary documents, or excessive polish. Don't automate waste.

3. Connecting the dots:

• Connect goals with everyday work. Make sure they have clear visibility into how and what they are doing is contributing to the goals of the company. 

• Outcome oriented. Ensure that the objectives you track are measured results and outcomes that align with strategy, not just activity or output volume.

• Deep customer understanding. Continuously learn from your customers. Deeply understanding their real problems ensures you stay focused on solving the right things. 

4. Leadership Practices:

• Dedicated thinking time. Ensure people carve out and protect dedicated time to step back, think and assess the bigger picture away from the daily firefighting and operational grind. 

• Learn and be curious. This means everyone in the organisation should always be seeking improvement and demonstrating curiosity about exploring new possibilities.

• Effective AI integration. Leverage AI's potential to boost efficiency, yes, but strategically. Ensure Tobi Lütke’s "reflexive AI usage" translates to applying AI effectively to amplify the right tasks and strategies, not just creating AI-optimised busywork.

The pressure to move fast and be efficient is immense and always will be. But speed in the wrong direction is worse than standing still. Drucker's words should remind you to question everything and focus on doing the right things. You absolutely must have a bias for action, but ensure the action is right, and when you learn it is not, the best leaders take that as a learning or input and move forward.

Building an impactful, valuable, and enduring company isn't just about doing things right; it's about having the clarity, courage and discipline to make the hard choices, say no more often than not, and do the right things. 

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