The art of asking for help

A lot of people, if not most people, take care to project an online persona of success and continuous improvement, but shy away from talking about unsolved problems and failures. I am going to try to be more intentional about painting a fuller picture of my learnings, including my screw-ups and subsequent learnings.

I have a few reasons for this:

• Failure is one of our most valuable teachers, so since I’ve already made the “investments,” I may as well scale the returns 😊
• I aim high, so when I screw up, I tend to screw up real good 😅
• I want to use my position of privilege and power to help normalize the fact that everyone screws up, even (and especially!) “successful” people; the key thing is to turn the setbacks into learning

The story

Note: I will anonymize some of the details both to respect privacy of individuals as well as to avoid talking about non-public IBM information.

Several years ago, the CEO of a high-profile SaaS company reached out to senior IBM executives to explore a partnership. After some top-to-top conversations, the senior IBM leaders decided that on our side the focus would be our Watson AI technology and I would be the executive leader. I was confident that I would succeed because I was an expert with the partner’s product and I had great connections with leaders there.

It didn’t go well. In fact, it was a shitshow 💩.

I won’t get into the concrete project problems because I want to focus on the meta-problem: I didn’t ask for help when it was clear things weren’t going well.

Stepping back: How I learned NOT to ask for help

When I was young, I read a bunch of books and sought out a bunch of mentoring on how to be successful as a software engineer and as a leader. One of the things I came to believe was that top engineers and top leaders have incredible persistence and never give up, no matter how tough the task.

Two examples:

1. When I was a coder, I’d iterate again and again on a design and implementation until I was satisfied it was perfect, no matter how long it took me.
2. When I was leading the rollout of GitHub Enterprise to IBM, we worked with GitHub to rearchitect the production system (twice!) in order to maintain our design point of a single scalable instance for the company, even though it was incredibly stressful.

Like all “successful” people, the behaviors that I associated with success became more deeply ingrained in my mind as the correct and only way to work.

And like any mindset formed by past successes, it’s great until it isn’t. And on the partner project, this mindset bit me in the ass, hurt me professionally, and hurt IBM.

Screwing up royally

In the early days of the partner project, I’d give my very demanding boss, an IBM General Manager, regular updates on all of the early progress and they were thrilled. But as the project proceeded and progress slowed, my updates slowed and then stopped altogether. To make matters worse, I had an upcoming checkpoint with the CEO of the partner company and the IBM SVP executive sponsor, and it turned into the worst meeting of my life as it was clear that while we’d made some technical progress on the MLOps lifecycle for the underlying data, we lacked a killer use case. The meeting was awful— I felt like I was playing tennis without a racquet 🙃.

Shortly thereafter, the partner relationship got transferred to another executive and they were eventually able to ship something OK but not great, partially because the partner company had lost confidence in us after my poor leadership of the project.

How I learned it’s OK to ask for help

My manager scheduled a 1–1 to understand what had gone wrong on the partnership and I was finally completely transparent about all of the problems I’d hit over the previous months.

My manager asked me “Why in the heck did you not ask me for help when you hit these problems and it was clear you were stuck?!”

I said “I don’t know. I guess because I’m an IBM Distinguished Engineer I feel like I should be able to figure this stuff out myself.”

They said “Are you kidding me?! I’m a General Manager—much more senior than you—and that doesn’t stop me from asking for help when I need it. As executives, we get put in charge of really hard stuff. If you never get stuck, it probably means you’re not being ambitious enough! If you find something’s moving too slowly or is stuck, and you can’t fix it pronto, schedule time with me and we’ll talk it through and walk away with a set of actions for each of us to help get you unstuck.”

The art of asking for help

Since then, I’ve taken my former boss’s advice re: asking for help, and it’s helped me take my performance to another level. Here are some things I’ve learned about how to do it well.

1. As always, timeboxing is your friend. For a given problem, give it an aggressive timebox as a defense against getting stuck and spinning your wheels. A timebox of more than a week is usually too long. Even if you’re working on something super-complex, create shorter-term milestones with dates to ensure incremental progress, and/or to help you realize more quickly you may be getting stuck.
2. The early professional mistake: Don’t ask for help out of laziness; ensure you’ve exhausted all of your creativity first (within the timebox, of course).
3. The senior / successful person mistake: Don’t wait too long to ask for help. If you’ve missed some milestone and exhausted all of your creativity, ask for help.
4. When you ask for help, whether digitally or in a meeting, be crisp on the problem definition, what you’ve already tried, and what concrete help you think the leader can provide to you. In my experience, great leaders will take this as a starting point and then improve upon your recommendations both because of their broader purview and different set of experiences.

The art of giving help

As an executive, I’m also on the other side of this. Here are some of my good practices.

1. Normalize that asking for help is both normal and good. You don’t necessarily need to write a blog entry about it 🤓, but you should explicitly talk about it as part of your leadership messaging. And as the saying goes, “When you’re getting tired of saying it, they’re starting to hear it.” This helps create the conditions for psychological safety.
2. Try to tune your leadership Spidey-Sense to be on the lookout for people who need to ask for help but don’t, either because they think they need to solve every problem themselves (as I did), or they simply aren’t good at timeboxing. If you sense this happening, repeat step 1 and ask some friendly but pointed questions to see if they are indeed stuck.
3. If someone does ask you for help, first of all thank them (and repeat step 1), talk it through with them, establish some concrete follow-up actions for each of you, and make it your highest priority to follow through— both completing your actions and then checkpointing until they’re unstuck. Actions speak louder than words, so while it’s important to say the right things (step 1), it’s even more important that you demonstrate both that it’s a high priority for you and that good things happen when folks ask for help the right way.

I hope this was helpful to you (no pun intended). Like everyone else, I’m a work-in-progress, so I welcome your feedback and suggestions.