Monthly Archives: April 2025

I was planning to start this piece with a quote about failure and resilience from Abraham Lincoln. He is my standby for such things. However, other than Jesus and Shakespeare, he may be the person in history with the most quotes improperly attributed to him.

Instead, I can sum up what I’ve learned about failing with this:

Lack of clarity – up, down, and sideways – leads to failure.

That isn’t to say clarity leads to success. Clarity points everyone in the right direction. You still have to do the work to make it happen and keep everyone aligned towards the right direction, making pivots when appropriate. But if you don’t start with clarity, you definitely will not get where you want to go in the time you want to get there.

Thus, what I’ve learned from failing are a few good ways to ensure clarity.

ASK. THEN BE QUIET. | or | BE QUIET. THEN ASK.

You may find yourself in a situation where you have an audience with a leader, maybe your boss or your boss’ boss, who has a vision or a strategy or a plan that you’ve had a chance to review and you’ve got questions. In this case, you ask questions and be quiet while they’re answered.

Or you may find yourself in a situation where the leader is presenting or simply stating their vision or strategy or plan, but it isn’t in writing. In this case, you’ll be quiet and ask questions when the time is appropriate.

And if you do not have a situation where you have an audience with the leader, get it. Then, ask questions and be quiet. It is very important at the outset you have clarity from the most senior person you can get an audience with on what their vision and expectations of you are.

Regardless, make sure you go into such a discussion with some set of standard questions you might use to ensure your own understanding of the current situation and desired outcome. Get as many of the questions out and answered at the outset.

And after you do this with the leader, then you need to go to your team and do the same. And then go sideways to colleagues at your level who are leading teams in other functions. Basically, you need the up, down, and sideways perspective of as much of the organization as possible.

Some leaders tend to jump to a solution, or feel they’ve done enough work to articulate what they think the solution is, and what your role in it should be. And they might be right.

When it comes to asking your team and peers, there tends to be the same type of behavior as with leaders. It’s important to see if what’s being articulated by your team and peers aligns to what you heard from the leader. Consistent alignment throughout is a good indicator of clarity.

You, however, should make no assumptions on what the situation is or what the situation calls for. Ask the questions of everyone even if you do know or think you know all or most of the answers.

And start laying the groundwork for the next steps. Ask who you need to go to in order to find data about the market, customers/segments, business analytics, CRM, martech stack, and whatever data is used to make decisions or create go to market actions. Ask who you need to go to about project management systems, documented workflows, process documents, and other systems and documents for how work gets done on the team and across teams.

Finally, and maybe most important, find out from the leader how they prefer to see strategy and plans presented to them – or if they prefer to be part of the planning process and want to see work in progress.

MAKE SENSE. DON’T ASSUME IT.

Unless you’re told otherwise, change of some sort, to some degree, is either wanted or needed. What has “worked” either isn’t working anymore, or is only addressing a part of a now evolving situation that you have been brought into address.

But you cannot address the best approaches to take without getting (1) as much data as possible about the market and the customers in the market (consumers and B2B, as well as relevant internal customers), (2) how the business currently goes to market, and (3) how the business – and your team – performs and is perceived in the market – and your team with internal customers.

Do not allow yourself to be dissuaded from finding the data you need. The data is there. Or enough data is there for an inquiring mind to build upon, cross-reference, combine, and then synthesize into the foundation of a strong story from which your strategy can be built.

Do not allow yourself to be pressured into creating a plan or making changes to the current state of things without allowing for the time needed to do this work. This is an important point in time where the old adage, “Sometimes you have to go slow to go fast” comes into play. That’s not to say you take all the time in the world here – you’re not looking for a “perfect plan”. But, more than likely, the situation you’ve been brought into is the way it is because something isn’t being looked at correctly or the right things aren’t being looked at through the right lens.

And since we’re on old adages, do not throw the baby out with the bathwater. While it is likely you are in the situation you are in to make change, there tend to be good reasons for why work is done the way it is done. Complete overhauls may be needed in some areas, but there will be areas where fine tuning is all that is required.

At this stage, it’s important that you take partners. Show your team how you do this work, what questions needed answered, how to synthesize different data, and assign some of it to them. Make it a collaborative process in some way with your peers and with those from whom you pulled data. Let them see what sort of questions you’re asking and how you are applying what you’re learning. It’s OK to have some debate and disagreement here. While you bring a level of knowledge and a different way of thinking, no one has the corner on smarts. Plus, taking the partners now will stress test your hypotheses earlier and make the work that lies ahead go more smoothly.

And if the leader, usually your boss, wants to be part of the process or see work in progress, let them see the questions you’re asking, how you’re applying what you’re learning, and what further questions you have. Let them provide guidance to ensure a tighter alignment later. I like to say I don’t want a strategy or plan to be a big reveal and a “Ta Da!” moment upwards. I much prefer it to be something with head nods and engagement already baked in.

RALLY ALL THE TROOPS. INCLUDING THE GENERALS.

Recall the last few things I mentioned when you are asking and being quiet or being quiet and asking. I said you needed to lay groundwork for what lies ahead.

I just referenced the importance of taking partners as you make sense. Notice that the partners are above you, your team, and your peers – up, down, and sideways. While upwards tends to be the most important audience for being able to execute your intentions, building up your team and ensuring alignment with your peers is what will make your plans truly powerful.

Set formal times to either workshop the plan or present the plan to your team and peers before it goes upwards. And get some partners in that presentation upwards as well. It sets a leader’s mind at ease to see a strong, cross-functional team aligned behind the clarity they’ve provided.

Regardless of the form or format of the deliverable, state your case in simple terms. Support your case with clear data points. Do it with the minimal amount of content or time required. If it comes across as obvious and simple – you’ve done some great work.

A great way to ensure clarity is to make things obvious and simple.

And clarity is the best first step to avoid failing.