Over the years, I’ve come to realize one of the most thought-provoking questions to ask a startup founder is, “How can I be of help?”
When I was a startup founder in my mid-20s, a number of people I looked up to started asking me this question. Replaying my vague responses makes me cringe today. I left them with no possible way to know how best to help me!
At first glance, the question seems basic enough, but it’s actually quite pointed and requires some deep thinking on the founder’s part. We have to have an understanding of who is asking this question, what the needs of the business are right now, and then creatively connect the dots.
“How can I be of help?”
- As a founder, you will often hear this question from people who are in a position to help you grow your business.
- A bad answer closes the door to further engagement. It asks for too much right away, or for something the person would likely do anyway. It gives them no meaningful way to help you.
- On the other hand, a good answer to this question is open-ended. It allows the other person to engage their creativity about how best to support your work. It plants the seeds from which a long-term relationship can grow.
Don’t Close the Door
An example of not making the best use of your answer would be something like, “I’m beginning to fundraise for my startup. Do you know any investors to introduce me to?” (Yes, those were my exact words, which I used many times.)
On the other hand, imagine if you answered with, “I’m beginning to fundraise for my startup. It’s really keeping me up at night with worry. It sounds like you’ve been down this road before. Do you have any wisdom to share with someone like me?”
The first answer doesn’t leave a lot of room for connection. Either the person (who, remember, you’re connecting with for the first time) knows investors who are top-of-mind to introduce you to, or they don’t. If they do, they probably won’t need to be asked. If they don’t, you’ve left them with no additional way to help you. It’s also a hefty thing to ask of someone who only just met you.
This question also assumes that investors are a monolith. In reality, after I pitched hundreds of investors in places ranging from angel investment group presentations to private, one-on-one lunches, I learned there is much more to know about an investor and why they invest, rather than simply whether they’re someone who writes checks for startups or not.
The second answer, however, can ignite a meaningful conversation that engages both parties. Being vulnerable about where you’re at and what’s challenging for you right now and recognizing that the person you’re talking to many have some wisdom to share makes for a totally different interaction.
Think about it: If someone in a position to help you asked what you needed, what would you say? Set aside your startup for a moment. Could you answer this question on a personal level from someone who wanted to offer you a hand in your personal life?
Operating With Intention
True power lies in thinking through your answer to this question before engaging with people you want to learn from. If you can’t articulate what you need, how would you recognize the solution if it came your way? If you think back to times you’ve helped someone with a challenge, lending a hand was probably a lot easier if the person could articulate what they were facing and why it was a challenge. If they could, then your fresh set of eyes and past experience probably ended up being invaluable to someone who was stuck on a problem.
A founder who pays attention to her business knows what she’s up against on a day-to-day basis. A creative and versatile founder knows how to connect the dots among the resources they have at-hand in order to reach a solution more quickly than if they had tried to solve it alone.
In my career, I’ve seen the value in having a clear intention before starting a conversation with someone I find intriguing. That intention could be wanting to learn more about a new city I’m visiting or meeting talented people I may want to hire. Having a challenge — or several — top-of-mind before engaging with someone I admire has been a game-changer for me.
Just one example of the transformative potential of a clear intention comes from my recent experience. From 2015 to 2019, I traveled the world full-time working remotely from my laptop. I changed cities, or even countries, every handful of weeks. One of my interests during this time was getting to know other entrepreneurs and founders. At first, it was a challenge to get traction in a startup community because I didn’t know where to start. I wanted to maximize my time meeting new and engaging people, but I was always the new person in a group.
Then, I started showing up with a clear intention of asking for help. If I met someone interesting at a coworking space or tech meetup, I would say:
“I really enjoyed talking to you! Is there anyone else in the startup community here who you like spending time with? I have a feeling if you like them, I might too! I would love to meet them if you’re up for making an introduction.”
More often than not, someone willing to have a conversation with a foreign visitor is also someone who is excited about networking. These hyper-connectors love making meaningful introductions! On the whole, this kind of request was well-received by people who prided themselves on growing their startup community by introducing two people who may share interests.
I was able to meet interesting people who I enjoyed learning from without frittering away time in a new city or country wondering who was a leader in the startup community. If you’re interested in getting to know new people who share your interests, asking someone who you already enjoyed talking to is a great place to start.
Set Clear Goals to Drive Intention
To come up with a great answer to the question of how someone can help me, I need to think carefully about the challenges I’m currently up against. For me, this becomes much easier when I regularly set goals. I set three small goals each day, between three and five weekly goals that are a bit bigger, and I’ve recently started setting major goals for the year ahead annually on my birthday.
Knowing exactly what I’m working on now and where I’d like to be in the future has made my interactions with people I look up to more impactful than they would have been had I been aimlessly drifting through each day.
For example, when I was traveling full-time, I often set goals each week for how many startup events I wanted to attend in the new place I was visiting. It was top-of-mind for me to be on the lookout for spaces where interesting entrepreneurs hang out to see if there was an event I might be interested in attending. Maybe a coworking space advertised a happy hour event each Friday, or a featured speaker at a meetup tweeted about a monthly female entrepreneurs dinner she hosted at a local restaurant. Having this goal as a guiding star throughout the week led to different results than I would have seen had I merely aspired to attend more events ... someday. It turns out that when I have a goal, more often than not, I keep my eyes open, follow new opportunities, and do what it takes to meet the goal.
Stay Specific
I have also found that having “How can I be of help?” in my back pocket when I meet new people is a great way to focus the conversation into action. I’m able to learn more about the person that I’m talking to and offer a hand.
It can be tempting to go vague. Don’t.
Sometimes newer entrepreneurs aren’t certain of an answer, and things can feel awkward. I noticed that I would bail when this happened by quickly ending the silence between us with, “No need to answer now, just let me know if something ever comes up.”
During the awkward silences, I would also find myself saying the meme-worthy phrase, “Let me know how I can be helpful.” It would slip out because I didn’t want to put the founder on the spot if they didn’t have an answer to my original question, “How can I be of help?”
But when I heard, “Let me know how I can be helpful” as a founder, I never felt like it was the start of a meaningful conversation. It felt like a door being shut, and it was usually the final thing someone said. To me, it’s the passive way of offering a hand. How many times have you reached out the next day to someone who offered, “Let me know how I can be helpful” before walking away to start a conversation with someone else?
If you ask this question and get a lukewarm response, don’t go back on your original, genuine offer to be of help. Instead, try offering an example from your own business or life to frame the question for them:
“Currently, for me, our team is struggling with finding a virtual assistant who has the skillet we need. Do you work with any virtual assistants? Or do you know anyone who loves their virtual assistant? I’m really curious to talk to someone who has found a great fit to learn more about how they did it!”
Don’t Just Ask Questions — Build Relationships
“How can I be of help?” when asked of founders in a way that leaves room for them to truly open up, can lead to a genuinely deep conversation that leaves both parties energized in the end. Being a founder can be lonely, and having someone who has walked the same trail offer genuine support along the way can be a lifesaver. Plus, asking this question gives you both a touchstone to check back on as your relationship develops into the future. Both parties know more about the other person’s experience and start building a mental association.
Take the example of the founder who is raising capital. Weeks later, the more experienced founder may be reminded of their counterpart who’s looking for a hand doing the same, emailing along a pitch deck template that someone shared on Twitter.
Likewise, let’s say that the founder who shared her fundraising challenge thinks back often to the thoughtful tips that were shared with her because they greatly helped in the fundraising journey. She may decide to introduce a new founder she meets to the more experienced one as someone who can provide great advice.
Asking a thought-provoking question like “How can I be of help” — or having an answer that makes the most of someone’s wisdom and experience — does not just make the conversation at hand richer. It can be a purposeful foundation for a new business relationship.
