Asking for opportunity

One of the lessons people regularly reference is having the courage to ask for what you want.

That’s a common theme in startups — and it applies in a lot of places, including more traditional workplaces, and in personal relationships. 

But asking for what you want doesn’t guarantee it’ll look / feel like what you expected, or that you’ll even want it when you get there. 

Getting what you want isn’t always a good thing

The secret to growth for most early stage companies is partnerships. 

Sometimes these are formal, like an OEM agreement that includes a split of any profits made. 

They can be informal too, like using growth or marketing tactics to promote someone else’s product, community, or content…often when there’s an explicit positive value in both directions (although that is not required). 

In larger companies, a partnership gone south can cost time, money, and lead to cutting employees. In the early stage it can mean the death of the company. 

Both of these are nightmares for project / product managers, who usually know from experience that signing an agreement is a lot different than delivering on it (in both directions). You may walk away with everything you wanted in a contract, and find that the cost to operations is much higher than expected over time. At large organizations, the CEO is usually long gone by the time this happens. 

And that’s just the business cost. Personal relationships, learning / growth, and feeling like you are making a positive contribution to the world are often casualties as well. You may walk away with cash, but few friends, a failed marriage, and/or deep depression. 

Asking for the opportunity is different than asking for the end goal

One of the things I always look for in a partnership of any kind is if the other person (or persons) understand the work at hand, and if so…whether or not they are willing to do it. Surprisingly, those two things don’t often align. 

What happens when you recognize the work you want to do is that you can the ask for the opportunity to confirm it, and to learn more about how you’ll fulfill it, how you’ll get where you’re going and what that middle ground looks like. 

A friend of mine did a nice job of explaining it recently in reference to their search for a healthy relationship / partner…

“If I am to attract my reciprocal at this point it is an independent, free thinker on an uphill from rock-bottom journey of self-discovery…who is practicing every day to be authentic and mindful and do the right thing with consciousness. I fail every day in some way but I am striving and aware at least. I get my issues finally…shedding light on them makes them [something I can work on]. I know we get what we ask for. Every single time I sit down and thoughtfully ask for what I want or need it is given. Right now I am asking for serenity, for peace, for growth, for the opportunity to know myself deeply, and daily to help me let go of what no longer serves me.”

This might sound deeply personal (and it is), so here’s a specific example for entrepreneurs / early stage companies that illustrates the difference between asking for what you want, and asking for the opportunity to work towards it. 

Another friend that runs her own business had a partnership lined up two years ago. It was huge, and would have tripled her incoming orders within weeks (she sells in the B2B space, high utility items but a long sales cycle). The partner had a user base and audience that wanted her product. They were itching to ink a contract worth well over $300k, which is a lot of money for a startup in its first year. 

She wisely asked if they would be willing to do a test run, as an insurance policy for both sides. They declined, citing a fast moving market opportunity, signed a contract with one of her competitors, and went out of business 10 months later because they’d made 2–3 similar big bets that didn’t pan out (the operations side / delivery turned out to be more complex than they’d imagined). 

This type of scenario is why good entrepreneurs focus on iteration, and why I practice and advocate for the lean startup approach. 

Most of the time you can choose between building a company with a strong core product / service, a loyal community, and make it defensible…or you can swing for the fences. Very few people have the talent and insight to do both at the same time. 

This is hard earned knowledge. In some areas of my life I’ve practiced this for a long time, in others I wake up one day and have a laugh at myself for how it was always there and I overlooked it. 

Here are a few examples of what that difference actually looks like…


“Hi! Great news, we’ve been watching what you do with the platform and have some improvements to announce that we want to know if you like” (expressing a want, doesn’t remove possibility for constructive feedback but lessens it)


“Hi! We’ve gotten some interesting feedback about our product and we’re doing some testing each week / month that we’d love your feedback on (e.g. is it working? does it help you solve your most important problems? if you could imagine anything differently or better, what would that look like? (asking for an opportunity)

Strategic partnerships…

Was good talking with you the other day — sounds to me like those 4,700 customers you’ve got who fit demographic for most active users of our product would benefit from our product. Let’s talk #s and figure out profit sharing.” 


“Was good talking with you the other day — sounds to me like there’s an opportunity to find out if those 4,700 customers you mentioned are a good fit for our platform. I have some ideas bout how to test with a few hundred to start, would you be interested in figuring out a way for both of us to confirm if a larger partnership makes sense?”

Personal relationships… 

“I need a partner who recognizes my emotional needs, and is willing to help fulfill them.” (not, on the surface, an unreasonable demand, but can be overwhelming) 


“I’m interested in balancing my emotional needs, and I’m curious to find ways that I can both express what they are and also make specific requests that you can choose to help with and/or that I can get met elsewhere as appropriate (if an aspect of a partnership isn’t a good fit, maybe there’s a better fit for part or all of your need elsewhere)