How Can You Lead If You Don’t Know Their Needs?

A case for curiosity.

Last week, I had an infuriating accessibility experience that I wrote about in a LinkedIn post.

In short: I spent about an hour and a half registering for a personality assessment, fighting with ridiculous timed CAPTCHAs and two-factor authentication processes, and fumbling through obtuse prompts.

Only to get into the assessment and be met with a completely inaccessible interface that 100% required a mouse. For a keyboard-only screen reader user, that was the end of the line for me.

I was forced to wait for sighted assistance. That meant waiting for someone else (my wife, in this case) to both be present and have 45 minutes available to spend helping me through the process.

The Then, I had to take another, similar assessment on a second website. The registration process was far easier, but I hit the same inaccessible interface and, once again, had to get sighted assistance.

The personality assessments weren’t just for fun. They’re required as part of my leadership master’s degree program. I’m supposed to analyze the results and what they mean for my leadership style. A task I literally wouldn’t have been able to complete on my own because some web developers decided to use fancy slider widgets instead of good, old-fashioned buttons.

So why am I telling you all this?

I promise it’s not just to vent (although it is a bit cathartic to complain about).

The whole, frustrating process made me realize something.

We can’t lead others if we’re ignorant to their needs

These personality assessments were designed specifically for leaders, managers, and businesspeople. Yet whoever developed them had failed to consider the diverse ways in which these leaders use the technology that enabled the tests to begin with.

That means somewhere along the line, a project manager (typically someone who leads a team) had signed off on the design of the technology without bothering to ask a simple question: can everyone use this?

Those project managers – those leaders – were ignorant to the needs of the end user. They only ensured that their tools were usable to the few people who developed them. Had they asked that one simple question, they would have realized that they needed to check with people from other backgrounds and who use other forms of technology. They wouldn’t have shipped a product that hadn’t undergone basic accessibility testing.

This principle doesn’t just apply to technology or product development. This concept is universal. The question may be a little different depending on the situation, but the idea is still the same.

We have to get comfortable asking questions

Back in March, I wrote about how curiosity is a vital aspect of leadership. Now that’s even more clear to me.

Think about it:

How can you coach someone to perform better if you don’t uncover what’s holding them back?

How can you lead a high-performing team if you don’t know each member’s strengths?

How can you help a friend if you don’t know what’s affecting them?

How can you serve a population if you don’t understand the societal barriers that are impacting them?

In some cases, you can do great work that has a positive impact on others, even if you don’t know the answers to these questions. If I had to guess though, that’s because you’re not exhibiting true leadership abilities.

You might be operating on a hunch, or on information that someone else handed you, or according to a long-established procedure that has just been the way things are done.

But are you certain that you’re doing what’s truly best for others if you’re just following orders or procedures?

To be clear, I’m not advocating for disobeying authority, flouting rules and regulations, or disregarding standard operating procedures. These things have their place.

I am, however, saying leadership requires more of us than simply adhering to certain processes or ticking certain boxes. It requires that we ask what the underlying issues are – doing a root cause analysis, for you managerial types – in regard to everyday situations.

Applying the theory

This is going to get a bit leadership nerdy for a moment, but I’ll try to keep this brief.

Transactional leadership theory says that leaders should provide rewards to people for a job well done, and consequences for poor performance. It’s a give-and-take, carrots-and-sticks method of leadership.

Servant leadership theory says that leaders should always seek to meet the needs of the people in their charge, which naturally helps them become better performers and have a happier, healthier work balance.

I’m going to paraphrase Simon Sinek here, because he beautifully illustrates the difference between these two styles.

Transactional Leaders: “You’ve been late every day this week, you’ve been missing deadlines, and your work isn’t up to your usual standard. I need to see improvement soon or I’m going to have to put you on a Performance Improvement Plan.”

Servant Leaders: “You’ve been late every day this week, you’ve been missing deadlines, and your work isn’t up to your usual standard. Are you okay?”

Which one of these leaders would you rather work for?

If I had a choice, it’d be the one who was curious about what was going on so they could uncover how to help.

Getting to the root

Ask any project manager and they could tell you three different ways to do a root cause analysis. They’re trained on how to look at a problem and ask questions or seek information until they uncover the root cause.

One of those methods is even known as the “Five Whys,” because you’re supposed to ask “Why?” at least five times until you’ve dug deep enough.

Example

Problem: Monthly client accessibility audit reports are consistently submitted two days late.

1st Why: Why are reports being submitted late? → Because the final draft isn’t ready by the deadline.

2nd Why: Why isn’t the final draft ready on time? → Because the accessibility testers are submitting their findings a day later than scheduled.

3rd Why: Why are testers submitting findings late? → Because they’re spending extra time double-checking their evaluations manually.

4th Why: Why do they need to double-check manually? → Because there’s no clear checklist or tool integration to validate WCAG issues systematically.

5th Why: Why isn’t there a checklist or validation tool? → Because the team hasn't standardized the process for reporting across different freelance contracts.

Root Cause Identified: Lack of a standardized reporting workflow and toolset for freelance testers.

End Example

We can and should be applying this level of curiosity to the people we lead – whether that’s at work, for an organization, or even just in our home lives.

Example

Problem: Employee has been late to work every day this week.

1st Why: Why are you late to work? → Because I’m having a hard time getting out the door on time in the mornings.

2nd Why: Why is it hard to get out the door on time? → Because my mornings have been chaotic lately and I haven’t been sleeping well.

3rd Why: Why have your mornings been chaotic and your sleep disrupted? → Because I’ve been caring for my mom after her surgery, and it’s been emotionally and physically exhausting.

4th Why: Why are you handling that all on your own? → Because I didn’t think I could ask for flexibility without being seen as unreliable.

5th Why: Why did you feel like asking for help would be viewed as a weakness? → Because in past jobs, I was penalized for not “powering through,” even when I was struggling.

Root Cause: A deeper fear of judgment shaped by prior environments, combined with current caregiving stress that hasn’t been acknowledged or supported.

End Example

Now, we’ll probably annoy the heck out of everyone if we ask them “Why, why, why?” all the time. After all, we expect people to grow out of that by the age of four.

But that doesn’t mean we can’t be curious and get to the root of the issue, so we can better help people. We can mix up the way we ask, what we ask, how we ask, and how we offer support.

That will certainly make us better leaders in the long run, because we won’t be operating from a place of ignorance. We’ll be operating from a place of knowledge, understanding, and clarity.

Sometimes, doing this digging uncovers hard truths like “not everyone can use this assessment, so we have to take the time to redesign it.”

Sometimes, those truths are even uncomfortable, like “I’m struggling because I’m caring for someone else, and it’s affecting my work life.”

But those difficult truths are arguably the ones that require the most attention, so we need to be brave in addition to being curious.

Whew, that was a long walk

It’s a bit of a strange connection between accessibility issues and leading with curiosity, so hopefully I didn’t lose you along way. If you made it this far and still have any clue as to what I’m blathering about, I’d love to read your thoughts in the comments.

Do you lead with curiosity, or is that a skill you could still use to develop? I’m sure there are times when I could be more courageous and ask questions that might have uncomfortable answers. Going forward, I’m going to be active about looking for those.

Hopefully, you’ll do that too.

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