How to figure things out without asking too many questions


Recently, an intern asked for a half hour of my time to get a little career advice before heading back to finish her senior year at college. I had a couple days to think about what I should say.

What tips could help her avoid some of the pitfalls I faced early in my career? What secrets could help her take some smartcuts that would accelerate her trajectory?

pablo (5)The time came for us to meet and she sat down, pulled out a journal and pen, and waited eagerly to record some sage advice. Such pressure to deliver!  I only had a few minutes so I boiled it down to two words – Think Deep.


[Sorry Grammar Gurus, I just like the sound of “Think Deep” better than “Think Deeply.” It feels more active like the sports phrase “Go Deep” but in a business setting]

Think Deep

I explained that her first job will probably involve a lot of tedious tasks. Most people start their career in an entry level job that requires staying “in the weeds” so that the details of the boss’s vision can be executed.

Every team needs someone like that. It’s an important role but it’s not the final career ambition for most people.

I explained that even in the menial tasks, she should Think Deep about why it is needed, how it affects the workflow, how others will use it when she’s finished, and if it could be done differently, more efficiently, or eliminated entirely and replaced with a much better solution.

Thinking Deep is Important Because:

1. It turns people into Linchpins:

You can only excel at something you understand. You can only improve something you’ve figured out. You won’t advance very quickly in your career if all you do is complete tasks as they are assigned. Instead, surprise and delight your boss by figuring out a way to do it better and you’ll find a smartcut to move up more quickly.

2. It builds confidence:

Not only will your boss appreciate the improvements you’re making, it will also prepare you for future growth. As you learn more about why things matter and how they work, you will gain confidence in yourself. The more you figure out, the easier it will be to solve the next puzzle and the next one until you realize you’re capable of making greater contributions in your career.

questionsBut there’s one big problem with thinking deep – you have to do some digging to figure all of that out. You have to probe and ask questions but that can backfire!

The problem with asking questions

Asking questions reveals your inexperience. It makes you feel vulnerable. And even though you’ve heard “There are no dumb questions,” asking too many of them might make you look weak and unqualified.

And then there’s the problem of your boss’s impatience. When work piles up and tasks just need to get done, your boss may not appreciate the delay that your questions cause.


When I was in High School Algebra, I asked the teacher why a particular formula worked. I was truly curious about the logic behind it and believed that I could use it better if I understood it more deeply (okay, this time I prefer “deeply”).

He was a great teacher but he didn’t see the benefit in explaining formulas or equations. “It just works so memorize it, use it, and be prepared to be graded on it!”

I wish I would’ve learned this lesson in High School – not the algebraic formula but the lesson that there is a downside to asking too many questions.  It took me about 5 years to realize that being overly inquisitive can hurt your career path.

My bosses, coworkers, and peers often took my questions as a sign of weakness. There are a couple particular scars in my memory when I was publicly ridiculed for asking too many questions about a project.

But I wouldn’t be where I am today if I didn’t Think Deep about everything I do. And I wouldn’t have figured anything out without asking questions. Thankfully, there is a way to Think Deep without looking weak. And this is the piece of advice I chose to pass on to this intern.

3 Ways to Think Deep without Looking Weak:

1. Google it:

So many questions have been asked and answered correctly online. Start there as often as you can. If you’re in a meeting and someone uses an acronym you’ve never heard before, don’t burn your rare opportunity to ask a question on that – google it first and save your questions for ones that are more thoughtful and specific to your situation.

The same is true for a term, phrase, concept, or even a person’s name that everyone else seems to recognize but you don’t have a clue. Don’t burn your questions on those. Jot these things down as they come up and google them when you get a chance.

This also applies to the company network, database, and intranet. Before asking a question, see if you can find the answer yourself somewhere on your company’s servers.

As a manager, I’ve always tried to be open to questions, but it’s a lot easier when people find simple answers on their own and save their questions for the more complex ones.

2. Ask your boss:

When a task is first assigned, if the timing is appropriate, ask your boss a clarifying question or two but be sensitive to her answers and body language. If it feels like you’re pushing your luck, back off – you might have a better opportunity to ask a follow-up question later. Better to wait than to be seen as a pest. Remember, you can always go to other sources for your answers.

3. Ask co-workers:

After you’ve learned all you can from your boss, consider asking a couple more questions of a coworker, preferably someone in another department within the company who has a similar role. That’s the safest bet of avoiding any repercussions from being inquisitive.

But be careful not to push too far with any one co-worker. Be as sensitive to the body language of your peers as you are with your boss. Make relationships with a lot of people so you don’t overburden any one of them with too many questions.

There are so many things I could have shared with this eager intern but, from my perspective, this is the lesson I wish someone had shared with me when I started out. I hope it helps her. If you think this could help anyone you know, feel free to share it.

What’s this have to do with Journey Mapping?

Maybe you’re asking what this has to do with Journey Mapping. That’s a good question. I would argue that the core, the essence of Journey Mapping is being intentional about everything we do. Think deep about each step in the customer’s experience so that we optimize it or replace it with something more effective.

In my opinion, the best Journey Mappers are those who Think Deep.

Here are a couple other recent posts about Journey Mapping’s impact on Employee Engagement:
See Me!!! 5 Ways Leaders can Increase Visibility for each Team Member
Superiority Complex – Imposter Syndrome’s Evil Twin
Customer Experience or Employee Experience – which is more important?

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