Asking for startup advice is a skill. You can teach yourself how to do it and you can improve with practice. I was very lucky to have had great mentors and advisors by my side when we started Workable. The most useful thing they taught me was how to ask for help, how to make it count, and how to give back. Learning this skill is a gift that keeps on giving.
For whatever reason, perhaps the exposure from Workable or this blog, I get a lot of emails from young startups, usually asking for advice on their business plan or fundraising. Cool. I love to hear new ideas and it feels great to help when I can. My time is limited, but I try to give 20 minutes to as many people as possible. Yes, it can be a bit tedious for someone who’s very busy, bu I’ve met some great people this way, I’ve found companies I ended up investing in and I’ve learned a lot.
I did notice though, that most people don’t know how to ask for help. So, here’s a little bit of meta-advice. A list of tips on how to ask for advice. It’s probably not the perfect list. But I promise you that if you do what I describe here, you will get way more value from each contact you make, and you’ll leave behind a good professional impression regardless of your business’ circumstances.
1. Be open and specific
Don’t be the guy who sends out a vague email saying “I’m thinking of some business idea and want to talk to you”. Talk to me about what? Do you want advice? Co-operation? Career mentorship? What are you up to? How do I know I can help? What kind of help am I expected to give?
When you send an intro email, be very specific about who you are, what you’re up to, and how you would like the other person to help. You can do this in two sentences. Watch this:
“Hi, we’re an early stage startup making recruiting software for SMEs and Steve suggested that you have a ton of experience selling enterprise software to small businesses. I’d like to show you what we’ve built and ask for your feedback on our marketing – we won’t need more than 20 minutes for an introductory call.”
It takes less than a minute to read this email and figure out what I’m asking for, if they can help and what they need to do to help.
2. Make it easy
Chances are you’re asking a person who’s busier than you are to set aside hard-to-find time to help with your problems. Make it easy for them to do so.
Make it clear you’re only asking for 15-20 minutes of their time at first. Say that you’re available at a time of their own choice. Offer to Skype or call them on their number of choice. Do NOT insist in meeting face-to-face for a coffee or at their office, unless they suggest it first.
Simply put, your attitude should be “if you have 20 minutes of your time that you’re willing to give to me, I’ll take it even if I have to call you while you’re walking your dog, hell, even if I have to come walk the damn dog with you.”
3. Show up
If you’re offered a meeting or call, take it. Duh? Who wouldn’t, you may ask. Recently I decided to allocate a time slot on Saturday afternoons for taking advisory calls like these. You’ll be surprised at how many people started declining or asking for a more convenient time.
If you can’t be bothered to follow through and show up, maybe you didn’t really need or want the help in the first place. Don’t give the impression of someone who’s prepared to waste other people’s time without being prepared to do their part.
4. Don’t give up easily
Busy people may take some time to respond. They may cancel or reschedule. This doesn’t mean they don’t care or that they’re unprofessional. (so long as they dont’ overdo it)
You are not being disrespectful if you send a couple of reminders. You can do it politely and show you care and are willing to wait and try again. Of course, if someone says “I can’t” or ignores you several tries, then it’s time for you to get the message. But better send one email too many than one email too few.
5. Do everyone’s homework
The burden is on you to make the most of the meeting. If there’s some preparation to be made, do it.
Send some information in advance if there is something to share. Send the meeting request. Add the other person on skype and send a polite “ready when you are” notice 5 minutes ahead of time. Thank the person who introduced you. Read up on the other person on LinkedIn. If you have specific contacts to ask for, find out who he may know beforehand (social networks make this easy).
Try to make it so that the other person can walk into a call with almost zero preparation and waste not a single minute on the practicalities – so that all the time goes into what you need to get out of the meeting.
6. Set an explicit goal
Two super important questions:
a) What do you hope to get out of the meeting?
b) What do you wish the other person remembers after the meeting?
Pick one answer to a) and one answer to b). No more.
Be explicit about them. Lead the meeting with the answers to these two fundamental questions. For example:
“Thanks for taking the time to talk to me. My main goal in this meeting is to understand if my company is ready to seek funding and if not, why not? I hope that by the time we’re finished you will know how to describe what we do in one sentence, in case you need to talk about us with a prospective angle investor.”
Very few people do this. Be one of those people, and you’re guaranteed to get more value from the discussion.
When you’ve given me a goal, I can instantly put everything you say into that context. If the question is whether your are ready to get funding, I won’t waste time asking for irrelevant things and I will evaluate everything you say in a way that tries to answer that question. If you tell me “remember this one thing” I know where to focus and I will carry the information you want me to.
7. Something worth fighting for
People who spend their precious time to help others rarely do it out of pure altruism. They do it because they find it interesting or exciting.
Entrepreneurs are the kind of people who would be running 20 companies if they had the time to. They love ideas. They love to entertain exciting thoughts. If you can get a mentor excited about some aspect of your project, run with it.
Give him the sense that this is something worth going an extra mile for. They may spend more time with you, offer to introduce you to other advisors, investors, partners. You can’t get this every time, but you’ll need to learn to recognise when you’re striking a chord with someone’s interests, and capitalize on it when it happens.
8. Follow up with your request
Always follow up. Even if the meeting was a waste of time, send a simple “thank you” note. It takes 2 minutes and it’s good manners.
During the meeting, make a note of follow-up actions and send a reminder. Often in an advisory call the advisor will vaguely or explicitly mention some things he could do for you. E.g. a person he knows that could be helpful. A company that might want to buy your product. Whatever. Send an email asking for a follow up on this.
Watch how easy this is: “Hey, thanks so much for your time yesterday. We learned a lot from our call and some of the ideas we discussed are very helpful in refining our plan. You mentioned that your friend mr. Stevenson is an expert in our domain. We’d love to talk to him. Could you send an intro email? I’m including a 2-paragraph description of our venture below this line, so you can simply forward it to mr Stevenson if he’s interested to find out more before taking an introduction.”
Neat. Now the advisor can honour his promise by pressing a few buttons on his smartphone the minute he received your email. (if he needed to remember the task and write his own description of your company he would “do it later” which is another way of sending “this email will be seen again in 2 months when I clean up my inbox”)
If that something is not an immediate ask, try something like “Thanks for offering to introduce us to potential investors. We are honoured at the suggestion. I will take the liberty to bother you once again when we’re ready to raise our next round.”
9. Turn every pass into a shot
Occasionally an advisor will take active interest and start throwing passes at you. An intro to someone he’s met who might be useful to you. A useful article. Whatever.
Never, ever, let these passes go to waste. Always follow up, even if they are not particularly useful at the time. Always give the impression that if I spend 2 minutes firing up an email intro for you, my time did not go to waste.
I’ve had the good fortune to have advisors who would send 5 or 10 such emails for me in a single week. Sometimes I had a hard time keeping up with them and following up.
I came to realize that this is partly the reason they’re successful, because they keep doing things, they keep emailing and following up and connecting dots. I started driven by the desire to honour their attention, and I ended up learning how to constantly turn passes into shots. Some of those shots ended up on goal. I guess, if I didn’t do that, they would eventually divert their passes to someone else, someone who wouldn’t waste a good ball.
10. Offer to reciprocate
You may think you can’t do much to help mr. Advisor because he couldn’t possibly need you. Maybe it is so, maybe not. Either way, there is no harm saying something like “hey, I have no idea what I could possibly do to return the favour but if I can ever help you out with something, don’t hesitate to ask”. The worst that can happen is that you cannot be helpful but you are polite and respectful.
Also, keep in mind that, people’s goodwill and interest are limited and fleeting. When you find someone who consistently helps you in meaningful ways, you should not assume this will go on forever. Find a way to create a long-term interest for the helpful person, in a manner that also motivates them to continue their contribution. Maybe you can offer them to invest in your company at a large discount, give them a symbolic (small) equity option, give them a seat in your advisory board.
These are not things to hand out lightly to anyone, but if you find someone who is truly and genuinely making a difference for your company, ask them directly and try to find a way to forge a lasting and mutually rewarding relationship.
