How to ask for what you want

One of the biggest, most simple reasons you're stuck is because you're not asking for what you want.

We've all been there. We feel like we're chasing our tail with a deal, every effort and every inroad we've paved for ourselves is blocked.

I recently had the pleasure of meeting an entrepreneur who is in it to win it. I'm not going to tell you who it is, so let's call him James. James is super smart, he left his corporate job to start his company, he's dedicated to solving an important need by creating a useful thing people actually want. And he is working on it every single day.

Winner winner chicken dinner right? Nope. There was a major problem.

James was stuck at one of those hard spot, a chicken or egg spot. He was not getting what he needed to move forward.

We've all run into this. It usually involves money. We need to grow, invest in something, pay someone, whatever it may be. But we don't have the money. The reason we usually don't have the money is because we are waiting on an investor or a customer who hasn't paid up. So we're stuck, we can't do the thing until we get the money, and in many cases the money won't arrive until the thing happens.

So we wait, we get emails about how busy they are, or excuses that usually involve them on waiting on something or someone else to move forward on their end. And so we wait, nicely and politely, because that is what we were taught to do.

But here's the thing, you've got a business to run, and people are relying on you, and actual things that matter are at risk.

At a certain point you're no longer waiting, you're being strung along, you're wasting time.

So what do you do now? You ask for what you want, (and you don't apologize either). If they say "yes," that's great. If they say "no," that's also great. No means you don't have to waste any more time waiting, and you can move on.

Why is it so scary for us to directly ask for what we want and need? 

Here's a real example (details changed) where I rewrote an email to an associate in a VC firm for James. The email was asking nothing (and would have yielded nothing) - but a few simple changes turned it into an email that got James a meeting with the senior partners of the firm in Silicon Valley the following week. An email that gets you on a flight is usually a good thing.

Recognizing and handling the "I've been busy" backburner email:



Sorry for the late reply (we've all been traveling) - I'm following up with the guys this week; how are things on your end?



What this email means:

Ron's email to James gives no information and asks for no information. It's a "you're not a priority, I'm back burnering you" email.

For a little bit of context, "Ron" (name changed) is an associate at one of Peter Thiel's (many) venture capital funds. Ron is not the partner, or the ultimate decision maker. This fund typically does Series A rounds (James is looking for seed financing), and is heavily interested in James' space, (Fintech). 

After some quick LinkedIn snooping, we made an educated guess about the partner that Ron reported to. Let's call him Partner Dave. :)

So James wrote this reply to Associate Ron. But before he emailed it, he sent it to me. Here's what it said:

Hi Ron,

Thanks for the reply. Things are going well! We are hustling through our development and are nearly there.

I've had to spend so much time on fundraising by means of meetings, demos, travel, conference calls, etc. (I'm sure you know this all too well) that I'm planning to close the round on the 31st so I can be back to being fully focused on product.

Let me know if there's anything else you need from me or if you would be able to make an intro to one of your partners and I'd be happy to do a conference call with you.



So, what's wrong with this email?

At this point, James wants to close his round on the 31st. At the time of writing, we were 1 week away. His product was nearly finished in development, and more importantly he had a team of contractors and team members in dire need of a few things, 1) Money and 2) Traction.

James could not waste a second more of his valuable time on fundraising if it wasn't going to yield these two things. Doing so could cost him his team. 

However, his product was nearly ready for market. James' product is for businesses, so the time it would take him to close a deal would likely be 90 days or more. He needed to start building a pipeline of potential customers immediately. And in my opinion, he was ready. So I rewrote his email to say this instead:

Hey Ron,

Things are going amazingly well. We are really hustling through the development and are nearly there. So close! 

We've done some pretty extensive research into your firm, and we might be a really good fit for Big VC Firm since we are training zebras how to invest and your firm specializes in investment in african mammals. While I understand you normally do A Rounds so we might be a little early, I personally really like the idea of building a solid relationship during seed, especially since we anticipate hitting the milestones quickly with all the customer interest we are getting, (list names of potential clients)

Do you work directly with Dave over there at The Big VC Firm? If so, I'd love to find a time to chat with both of you directly. How does a quick call tomorrow around 10am PST/Noon EST sound?

Immediately after sending this, James sent a LinkedIn request (personalized of course), to partner Dave. Within 24 hours of sending this email, James had an email back. In less than a week he was on a flight to pitch their senior partnership at the fund.

I believe this email was effective because:

  • We kind of forced the issue of having James talk to Ron, but were still polite. I am putting him in the position to either say, Yes or No. He can either move James through the funnel or not.
  • We suggested a day and time to talk. So rather than saying "Do you want to talk?" a question most people's knee jerk reaction to is "No." We asked a question that is easier to say Yes to.
  • We built James' case. We explicitly stated why his company was a fit for Big VC Firm.
  • We presented the subtle threat of removing the potential deal. They could either act, or not.
  • Immediately after sending, James reached out to connect to Senior Partner Dave on LinkedIn. Sending him a personalized message and let him know he's been talking with Associate Ron. Partner Dave probably got the LinkedIn invite almost immediately (VC's are glued to their phones), and then later in the day or soon after, Associate Ron probably asked Partner Dave if he wanted to meet James. We facilitated two points of contact within a short timeframe.

This is all great, but now for brass tacks:

Operating with the basic understanding that in VC firms, associates report to partners and partners are the ultimate decision maker. Associates are in charge of "deal flow" which means having a lot of viable, interesting start-ups on their radar at any given time. Partners are in charge of pipeline, which means the start-ups that are actually going to be considered for investment by that firm.

My rule of thumb with so many things is that whenever something seems confusing or doesn't add up in any situation, always look for the money. In this case, associate Ron wouldn't be doing his job if a viable deal dropped off before making it to pipeline. So when James mentioned taking away the deal, Ron had to act. (Assuming James' start-up was considered viable by Ron).

By doing this, James was able to slightly shift the balance of power back to him.

You have to ask for exactly what you want, so that others know what to give you.

Most people don't explicitly ask, assuming that people know what they want. In reality, we have no idea. Social media posts that prompt readers to "click" "read more" or "download" do much better than those that simply talk about the content and assume readers will understand that you want them to click through.

We are often wary of asking for what we want, because we are afraid we are asking for too much. In reality, we rarely ever are. Oftentimes, people find it very refreshing to be asked directly for what they want, rather than wonder about their intentions.

5 Golden Rules to Asking for What you Want: 

  1. Always, always, always be polite, respectful and courteous.
  2. Never ask for something that you know they are not willing to (or can't) give.
  3. Always be open to flexibility and negotiation in your ask, and make sure they know this.
  4. Always be open and forthcoming about all pertinent details they will need to know to properly grant your request.
  5. When the timing is right, just ask. Even if you don't quite feel "ready." Timing and the way you word your request is more important than anything else. 

Is there anything anywhere in your life that is stuck that you could apply the following thinking to and make a concise but polite ask? Tell us about it on the Facebook Page