What a $15,000 Thumb Drive Taught Me about When to Ask for Help

How much do you think you'd be willing to spend on a thumb drive – the kind you might get for free at a conference? Ten, twenty bucks? Maybe a little more for serious memory and/or a bottle opener?

How about fifteen grand? And no, there's nothing special about it. Not a trick question. 

If you're thinking, "I wouldn't, but you seem dumb enough to have done that," you are correct -- for the most part. Here's how it happened and what it taught me about how to ask for help:

Many years ago at the startup where I first got my feet wet in product management, the CEO decided it was time to engage a public relations firm to get our name out there. I knew next to nothing about PR, but I was excited because, hey, startups need publicity. Our product was still in its infancy, but as it turned out so was our conception of what the future of the business was.

It's also relevant to point out how young and naive I was at the time. For instance, I was easily dazzled by the polish and style of the PR folks: Their pitch deck is bound in hardcover! They have cocktails at lunch! Their haircuts are "American Psycho" good! We signed with a reputable international agency, and so I assumed it was only a matter of time until our company was a household name and I would be giving my TED keynote talk on how to be awesome.

Spoiler alert: There is a vanishingly small chance you know of that product. I also remain uninvited to the TED stage.

The problem was that we weren't at all ready to get that kind of help. We didn't know what we wanted our product, much less the business to be in the long run. Turns out that's pretty important when you hire people to tell the story of your company. Our PR people went half-crazy trying to get us to stick to a single story so that they could figure out what the hell to tell people about us. Our CEO thought the tech was sacred, as did the rest of us, so we resisted seeing it dumbed down for broader consumption. After chasing our tails for a while, we mutually decided to end the relationship. Later, we joked that all we had to show for the $15,000 invoice we paid were a few thumb drives branded with the PR firms' logo. 

Now and then in the years that followed, we would refer to half-baked or bad ideas as $15,000 thumb drives...usually followed by that "Ha ha...ughhh" groan. If there was one benefit from the whole fiasco, it's that it gave us a good, if costly and embarrassing lesson in how and when to reach out for help from others.

Not all Requests for Help Are Created Equal

When I come across columns like this one about how asking for help is a sign of strength rather than weakness (or this one, or this one), my reaction always starts with, "Yeah, but..." It's true that when you need help, you should ask. But, and maybe this is a generational thing, more often than not what I see from younger colleagues at least is a tendency to ask for help too quickly. And yes, there is such a thing. At my former company, we asked for help from PR experts before were ready, and all we did was waste a lot of peoples' time. 

There are no absolutes in life, and asking for help isn't always the right move in the moment. You can do it too quickly or too often and undermine your credibility in the process. I'm not an advocate of trying to do it all yourself -- I've relied on the help and advice of many people building UserMuse and preparing it for launch. But just like saying "I don't know," not all ways of asking for help are created equal.


If you want to get the assistance you need without either undermining your credibility or burdening others unnecessarily, here are a few points to keep in mind:

  1. Do your own thinking. You should be the first person to break a sweat. There's a difference between asking for help because you're stuck versus not having tried yet. I get annoyed when people come to me with questions and I have to go through the whole, "Have you tried x? You should try x. I'd have expected you to start with x. Go do x." It's annoying, especially when people make a habit out of asking for help as a way of getting other people to do their thinking for them. On the other hand, when someone comes in with an interesting problem and they've done their homework, that's a worthwhile place to engage. 
  2. Get your story straight. Clarity of thought on your part is important. If you can't explain what you're doing or don't know what you want, how can you expect people to help you? Sometimes I've wanted to grab a person by the ears and repeat this to them.
  3. Don't share half-baked ideas. This is something I still try to police myself on regularly, because I'm prone to over-excitement about ideas and jump up to bounce them off someone right away. Lots of times, we ask for help not because of a problem, but because of an idea we get excited about. Taking what you think is a big idea to your boss or a colleague can be exhilarating, but it's still worth slowing down and thinking it through. If nothing else, you're less likely to waste someone's time. Whether it's a few hours or a few days, I've never regretted taking a little more time to think about an idea at work.
  4. If you're not ready to listen, don't ask for help. Back to the $15,000 thumb drive again, we sought the advice of PR experts, but we were totally unwilling to listen to their advice. We wanted them to listen to our ideas, and we weren't open to theirs. No wonder we get nothing out of it. If you're not at least a little bit prepared to be wrong, then you aren't ready to ask for help.

I agree that asking for help is a sign of strength rather than weakness. Being prepared to receive it is an even bigger sign of strength.