Reflections on Achieving Your Goals: Don’t Sabotage Your Wins

Constant dropping wears away a stone

And paper cuts can kill you…

Most people are focused on the big, challenging and shiny projects, and that’s important. However, while we’re driving the big blocks and highly visible deliverables, we must not drop the ball on the more mundane promises we have made (e.g. project updates, the task we promised our co-worker, newsletter updates, that email from our boss,… – you name it).

Don’t undermine your big wins by being sloppy on the small and mundane tasks.

The problem with (many) little misses

We all miss something every now and then. That’s normal and ok. The problem arises, when it happens repeatedly, so that people start assuming you will miss a promise with a high-enough probability. They will lose trust in you and your reputation will erode. Once it looks like a pattern, you have a problem that you must solve.

Bringing in the big wins and celebrations is awesome! Be proud of it! Others will see them and recognize you for the achievement.

However, if there are small misses sprinkled throughout the big wins, people will remember the constant small signal much more than the sporadic big signal. What would you remember more, if I brought you a nice hot latte every morning or a $100 bill once a month? No, sorry, I won’t do either, it’s just a thought experiment.

Visibility is in the small things. If they don’t create confidence, we have a problem. Little mistakes add up and can neutralize all the good stuff you worked so hard for.

As managers, coaches, or even parents, we all know the situation. We want the best for our employees, coachees and kids. We want them to stack up wins. As we watch them over the weeks we all too often go: “Nice, nice, nice – oh shit, WHY did they do this?”. Then we start back from square one.

Tactics to Avoid misses

On the highest level, there are three key strategies to avoid creating a pattern of little misses:

  • Accountability: Track your promises – This is the most basic and simplest one. If you sign up for an action item, write it down right away. Block time in your calendar. If you can’t do it, say ‘no’ right away (read that Friday musing). No excuses after that.
  • Quality: Slow down and double-check – Don’t just try to get rid of an annoying task. Chances are you will miss a key point or your numbers or answer won’t make sense. Usually one of two things will happen as a result: either you will look like you don’t know what you’re doing, or an escalation will happen further down the road. You don’t need either.
  • Comprehensiveness: Ask yourself ‘what am I missing’ – The most frustrating thing for a (senior) leader is to have a question or count on a deliverable and then getting something that doesn’t solve the actual problem or answer the core question. Now the leader has to spend time following up and chasing down what you need. Prevent that from happening. As yourself what you’re missing and what the logical next question would be.

A word about managing senior leaders

Senior leaders have to fight a hundred fires at any given time. They need to constantly switch context between vastly different problem spaces. In meetings that is every 30 mins, in their inbox it is from email to email (i.e. within seconds). They don’t have all the details you have, and they might have forgotten a detail you shared a few weeks ago. They need to compartmentalize problems, quickly switch their thinking, recreate the full context of a new problem, get issues solved on the spot, and move on. Hundred times a day.

If they are not super-efficient with getting into a new context, understanding the problem and proposed solution on the spot and moving on, they will drown. Because of that, they usually have a very allergic reaction to anything that lacks context, is not thought through, doesn’t add up or leaves key questions open. Unless specifically booked, they don’t have time to brainstorm with you.

Understanding these constraints, here are critical things to do when responding to senior leaders:

Provide context – Don’t make them have to follow-up with questions to understand what you mean.

Be concise and crisp – Don’t make them have to search the answers to their concern in vast deserts of random data and words.

Close all loops (or at least provide timelines for when they will be closed) – Don’t make them continue keeping the topic on their worry list.

Get it done in your first reply – Don’t make them have to continue context switch in an email brainstorming conversation over days.

Double-check – Put yourself in the shoes of the recipient. Go over your answer and pretend to not have the context. Does is still make sense? Does everything add up?

Understand the intent

In order to achieve the above qualities in your response, specifically ‘getting it done in your fist reply’, it is key to not just answer the question at face value but to understand the intent.

Don’t just answer the immediate question or drop the data. Understand the intent! Ask yourself: “What is the requestor trying to achieve?”.

Once you understand the intent, what the requestor wants to achieve, you get a better sense of what additional information or context they might need. What additional questions were not asked but are required to achieve that intent? Provide the answers proactively!

Now make it consumable. Structure the data such that it serves the question and the underlying intent and the flow is easy to follow and understand.

Here’s an action for you

Spend a minute to reflect:

  • What action items and promises to others did you miss the last two weeks?
  • How may email threads with leadership did you have that required multiple inquiries and follow-ups from the leader?
  • How often was the quality of content not where it should have been for a review because you haven’t thought it through deeply enough?

What can you do to avoid and change that in the future!?


Did you like this article? Want to read more?

I will keep posting articles here and I have them lined up way into summer 2020. However if you want to get it all in one comprehensive, structured, and grammar-checked (!) view, check out our new book:


Put on your oxygen mask first - book cover

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