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7 Questions to Ask Before Committing to a Business Collaboration or Partnership

7 Questions to Ask Before Committing to a Business Collaboration or Partnership

A lot of people will tell you that business partnerships are like marriages. They’re right, in many regards: they’re a long-term commitment; the best ones are built on a foundation of deep trust, openness and respect; and you end up spending an immense amount of time together, so if you don’t like each other an awful lot, they tend not to end well.

At worst, they go down in flames. And the fallout from a bad business breakup can be miserable: unmet expectations, resentment, one person running off with all the money… basically, all the worst aspects of those group projects you had to do in school, except with cash and public reputations at stake. (I could tell you some horror stories, but that’s not the point of this post.) At best, though, you gain an expanded skill set; creative give-and-take; an expanded network; and perhaps the most under-appreciated upside, camaraderie as you build, succeed, fail, and bounce back together.

So how do you maximize the upsides and minimize the risks of the whole thing falling apart? As someone whose career has featured more than a couple of partnerships and collaborations, I’ve learned there are a few key questions to answer if you want to enter into a business arrangement with clarity and confidence, beginning with one you must answer for yourself:

1. How much psychological safety exists here?

Harvard Business School professor Amy Edmondson MIT Sloan School of Management professor Edgar Schein coined the term “psychological safety” to denote a quality that Google and other companies have discovered is foundational to team success: it’s a “shared belief held by members of a team that the team is safe for interpersonal risk-taking,” and “a sense of confidence that the team will not embarrass, reject or punish someone for speaking up.”

When you’re considering making a serious commitment to a business colleague, this is the first and most essential question to consider. If your answer isn’t an enthusiastic one, you may just need more time to build trust, or it could be a serious red flag.

If you think it might be a red flag, do not pass Go, and do not invest $200 (or $200k). And if you need to build more trust, consider making a short-term, temporary commitment instead: sign on for a joint project that will allow you to test the waters.

On the other hand, if you’re confident that you and your prospective collaborator score high marks for psychological safety, then it’s time to sit down together and explore some deeper questions.

7 questions to ask before committing to a business partnership or collaboration

There are two layers to the discussion: figuring out the logistics of working together, and gauging how much ease and flow exists between you.

A note on process: You might not want to tackle all of these in a single session, but I definitely recommend discussing all of them. Set aside a generous chunk of time, pair with food and/or a beverage of your choice – personally, I think nothing beats doing this over a glass of good red wine or a cocktail, but that’s just my taste – and take turns asking and answering.

Remember: if you encounter any surprises that give you a sinking feeling, that doesn’t mean you can’t collaborate on something short-term and well-defined. And it certainly doesn’t mean you can’t remain friends. It just means that you’ve identified important concerns that need to be addressed before making a bigger commitment. This is a good thing! It’s like the “Do you want kids?” conversation; if you have different answers to that question, then you either have some intense negotiations ahead, or you know to save yourselves further heartbreak by stringing each other along.

OK, on with the questions.

2. What is our shared purpose?

Have you taken the time to articulate your common vision, and make sure you’re both on the same page? If not, now’s the time.

I can’t tell you how many business partnerships I’ve seen go south because the partners had different ideas about where they wanted to go, but just assumed they were on the same page. And I don’t mean shared goal, as in the concrete thing you’re building; I mean, what do you want the impact of that achievement to be? Where do you want it to take you?

3. What skills and resources do each of us bring to the table?

If you were an heiress and you were getting married to someone of modest means, someone in your circles would advise you to sign a pre-nup. And in business partnerships, the same principle is true when it comes to financial investments. But when you’re dealing with intangibles – the size of your mailing list, say, or the fact that one of you has ten years’ experience to apply to building and coding the app you’ve dreamed up together while the other is just starting to teach himself to code – it can be harder to quantify.

Nevertheless, if you want to avoid resentment and difficult conversations down the road, it makes sense to make an inventory of the resources you’re each bringing into the collaboration, and having a frank discussion of the implications for how you’ll be proceeding. You might decide to adjust the distribution of profits or shares to reflect the difference in investment. (For more on that, see Question 7.)

4. What roles and responsibilities does each of us want to take on?

This is often one of the first conversations that takes place between prospective collaborators – “I could do this, and you could do that, and together we’ll take over the world!” – but it’s worth spending some time itemizing all of the work that needs to get done in order to reach your initial goals, and who’s going to do what (and what, if anything, you want to outsource).

This is your chance to be 100% clear about what you’re most excited about doing, what you’re willing to do short-term or in a pinch, and what stuff is totally out of your wheelhouse. It should be a clarifying, trust-building, and energizing conversation.

5. What does success look like for each of us?

What kind of financial return do you need in order to call this a success (or at least, not a complete failure)? What returns would constitute exciting levels of success? What are some other measures of success – such as gaining experience & expertise, exposure, etc.?

And if this thing takes off, what’s your dream scenario? Is it short-term or long-term? What would growth look like? What else do you picture in your mind’s eye when you think about a successful outcome?

6. How much time and energy can each of us commit to this project?

An overly-optimistic answer to this question has sunk many otherwise promising partnerships. Think back to those group projects in school: remember how much last-minute scrambling you had to do when other people mismanaged their time? The worst.

Nobody wants to be the one pulling all-nighters to make up for someone who over-promised and under-delivered. And nobody really enjoys being the disappointer, either.

So be realistic – cautious, even. What can you truly commit to? Give that. And listen for potential mismatches between the needs of the project and your capacity to work on it.

And finally:

7. What does a fair and equitable distribution of shares (or share of revenues, if you’re not going to incorporate) look like?

For this, you’ll want to think hard about the relationship between each person’s skills, time commitment, the resources they bring, and what they’re expecting to get out of it. (Notice how I’ve been cueing you up for this with the preceding questions? Soooo sneaky.)

This can be a minefield of a question, so I suggest tackling it this way: first, start by considering what you think is a non-negotiable percentage for the other party. What’s the minimum you would consider fair, given what they’re contributing to the partnership? Next, what’s the most you can imagine offering them, without feeling like you’re giving too much away? Now you’ve got a range in mind.

Then do the same for yourself: what’s the low end of your comfort zone, and what’s the high end?

Once you’ve both taken this approach, write down your numbers and show each other what you wrote. Odds are, if you’re simpatico, your ranges will be pretty similar, and you can negotiate within a pretty narrow window, which should minimize your discomfort. And if it turns out you’ve written down very different numbers, then that’s fodder for a bigger conversation about assumptions: go back through the preceding questions and make sure you’re 100% clear on what each partner intends to contribute.

While this conversation may seem tricky, my bottom line is that the people I do business with must have clear boundaries, and be able to speak directly about what they want out of the relationship, while respecting my needs as well. That doesn’t preclude having an emotional and intuitive layer to the relationship, but it does mean taking the time to communicate clearly and to be clear about what’s entailed in making a business partnership work.

And there are two layers to the discussion: the surface layer, where you’re answering questions and getting clarity on what each of you is contributing and expects to take away; and the emotional/energetic layer, where you’ll be sussing out how easy it is to talk about these kinds of things, and whether the discussion is respectful, positive and generative. You want both things in any business partnership: clarity on the logistics of working together, and ease and flow in the relationship between you.

The Untenable End Game of the Personal Brand

The Untenable End Game of the Personal Brand

Four years ago, I made the transition from running a company with employees to going it solo. I spent some time considering company names for my new business, but in the end I decided that the simplest option was the best, so I registered and started building an online presence here. It has always stood at the intersection of personal and professional, as the work I’ve been doing – coaching, writing, teaching – is more personality-driven than my previous roles.

However, as I’ve moved deeper into the world of personal brands–where individual people market themselves with all the careful curation and business savvy of large corporations–I’ve become more and more skeptical of the kind of culture we are contributing to. Because as a higher and higher percentage of people become self-employed, and presumably take to the web to promote their services, a dystopic vision begins to form in my mind:

Seven billion personal brands. What a complete and utter nightmare–for everyone.

Picture the vitamin aisle in your local supermarket, and how overwhelming it is: the dozens of options for Vitamin B or probiotics; the hundred bottles of multivitamins, which you have to pick up one by one to find the one with iron or magnesium or whatever it is your doctor told you to look for.

Now imagine that there are seven. Billion. Options.

I mean, OK, I’ll grant you that every single person in the world is not going to be selling what you’re selling. So let’s make it a smaller number. Let’s be really generous and say there are, I dunno, 1,000 different kinds of freelance jobs one could perform, and that maybe half the population is employed at any given time, 40% of whom are self-employed. That would bring it down to 1.4 million people competing in every category. (Admittedly, this is extremely rough, back-of-the-napkin math, but bear with me. The exact numbers don’t matter so much as the broader brushstrokes.)

Using our analogy, that means in order for you to buy a jar of vitamins, you have to confront 1.4 million options. Talk about decision fatigue.

It’s an exhausting prospect for consumers, and equally exhausting for those of us trying to build a personal brand. Frankly, I don’t want to have to compete against 1,399,999 other people doing roughly the same thing I do, I don’t want to contribute to the online equivalent of the vitamin aisle. The mere idea of it makes my skin crawl.

An Alternative to Vitamin Aisle Overwhelm

Let’s shake the image of the vitamin aisle out of our heads, and replace it with something that’s human-scaled, aesthetically pleasing, and designed for connection: the farmer’s market. Farmers’ markets are one of my happy places: invariably, when I get to one, I have serendipitous meetings with friends and neighbours; my thirst for beauty is slaked; and I’m so surrounded by healthy and delicious options that I wind up eating well all week. And of course, in the process, I get to meet the people who grew my food, learn about how their seasons are going, and get new recipe ideas along the way.

Those are my benchmarks for a delightful shopping experience:

  • Beauty
  • Delight
  • Serendipity
  • Connection
  • Manageable scale (i.e. no decision fatigue)
  • Sustained value (i.e. I feel good about my choices afterward)

…and those standards hold anytime I’m having to shop for things (which, as the primary parent in our household of four, is pretty often).

Now, keeping those standards in mind, let’s return to our Personal Brand / vitamin aisle dystopian nightmare–and how to avoid it.

Marketplaces have sprung up to help consumers find the right match for their needs, in a variety of contexts: AirBnB leads the way in temporary accommodation; Etsy handles handmade and vintage goods; dating sites help you filter through staggering numbers of potential mates and hook-ups; Apple and Google have app stores. And Amazon is arguably still the leader when it comes to finding books and other goods; I regularly rely on its recommendations engine.

There’s no such marketplace for the work I do. But imagine if there were.

What if you wanted to find a coach or consultant who could help you develop your leadership skills, expand your team, or improve your health? You might have a few filters: maybe you prefer someone with experience in your industry; with a certain amount of experience; and within a particular price range. Perhaps, like some of my clients, you prefer someone who can meet face-to-face, in which case geography becomes important. These are all relatively trivial things to build into a database-driven site or app.

And from the coaches’ perspective, would it not be a relief to let someone else do some of the marketing, some of the time?

The same is true for the world of online courses.

It feels like everyone and their podcast microphone is launching an online course these days, but how the hell do you pick one? Comparison shopping is pointless, because everyone shares different information, and besides, the number of options is simply too high.

This is a much more crowded space already – edX, Coursera, Udacity et al. are tackling this problem, although they are focused primarily on university-type courses rather than personal development, and they are also learning platforms themselves, rather than simply marketplaces. I’m very curious about what might emerge if you gathered together a bunch of independent teachers and invited students to provide reviews of the courses they’ve taken, like a kind of Yelp for online learning. We might learn things like:

  • How much of the course did you complete? (Or did the materials languish on your hard drive?)
  • How would you rate the value of the content?
  • Who is best positioned to receive value from this course?
  • If you’ve taken other courses on this subject, how does this one compare?

I, for one, would love to know that since I loved Randi Buckley’s “Healthy Boundaries for Kind People” course, I might also love Lianne Raymond’s “Cherish.” Or that if I’m primarily an auditory learner, I might appreciate so-and-so’s teaching style. Or that Jen Louden’s “TeachNow” is the #1 ranked course on teaching, or that Tanya Geisler’s “Step Into Your Starring Role” is the Editors’ Choice for anyone wrestling with the imposter complex. And so on.

(None of those are affiliate links, by the way.)

As a teacher, I would also love to know who else is teaching courses in my areas of interest; how they’re approaching their subject; and how I can better differentiate my offerings. This feels like a win-win-win, to me: better clarity for students; more efficient marketing and promotion for teachers; and at least a modicum of accountability for everyone (in the form of reviews, standards for inclusion, and so on).

It’s important to note that I don’t think the solution is necessarily curation in the sense of publisher-author models or tying people into a particular delivery model. I prefer vendors to maintain their own approaches when it comes to course platforms and coaching methodologies. But I think online marketplaces offer some interesting possibilities here in terms of models that could be adapted.

I’m sure there are limitations to the way I’m seeing this question – and heaven knows the App Store has many, many flaws, as do Yelp, AirBnB, Etsy and the rest – but if anyone out there is trying to tackle this problem, and avoid the hellscape that is the Find-a-Coach Vitamin Aisle (or the, I dunno, Online Course Towel Department at Target?), I am all ears. Because I am tired, tired, tired of this personal brand situation, and I am ready for some better options.

Author’s note: While I’ve been mulling over the ideas in this post for many months, I want to give props to Jonathan Harris’s excellent essay, “Modern Medicine,” and particularly the section “Healers and Dealers,” which succinctly and elegantly articulates the distinction between marketplaces and attention economies – something I’ve spent over a thousand words rambling about here.

A Love Note to Entrepreneurs Feeling The Fear

A Love Note to Entrepreneurs Feeling The Fear

Dear You,

I recognize the place where you’re standing right now. It feels like a precipice, or a thunderstorm, or like being crushed under the weight of too many expectations and responsibilities. You feel like maybe, just maybe, your business isn’t going to make it through this.

And you might be right. But I want to talk to you about surviving this moment, and about what comes next.

The Fear is a Liar. You’re Not Alone.

First, it’s important that you know this: we’ve all felt The Fear. Starting a business is an inherently risky move, and the risks never disappear into the sunset — they only change. But it’s easy to feel alone when The Fear comes on, because that’s fear’s superpower: making you feel alone and vulnerable. So if you’re able, remember that every entrepreneur that’s ever entrepreneur-ed has felt the way you feel right now.

I’m telling you this because I got an email from a coaching client last week that read, in part:

“Will this ever feel easier? Will there ever come a time when things are running smoothly, my future & finances don’t feel debilitatingly uncertain, and I actually feel like I know what I’m doing? In your experience of living this entrepreneurial life, does it ever feel even just a little bit easier?”

I wanted so badly to write back a sunny, “Yes! It gets so much easier.”

But that would have been a lie.

So I wrote this instead.

It’s a letter to that intelligent, soulful visionary who wrote to me, and it’s also a letter to my younger self — for all those times when my doubts clouded over all certainty and confidence.

What Are You Afraid Of?

While our culture — especially the braggadocio-fuelled culture of North American entrepreneurship—worships at the altar of “pushing through” fear and ignoring emotions, the truth is your feelings will find a way to express themselves, either directly or indirectly. I strongly prefer understanding my own emotional weather patterns so that I can engage with them consciously, rather than letting them make unconscious decisions for me.

The big secret to this is simply: feel them. Allow the feelings to rise up—and if you need to, set a timer, as Chris Dierkes suggests, so they don’t overwhelm you — and give them a chance to tell you what’s up.

Karla McLaren, author of The Language of Emotions, says that fear’s job is to wake us up to something we need to be alert to. When we feel fear, she says, our job is to ask, “What action should be taken?”

I find that when I’m deep in the midst of fearful feelings, I need to start by asking, “What am I really afraid of, here?” That helps me get to the root of it before I shift into asking “What action should be taken?”

Either way, the goal here is: feel it, engage it, and work with it to gain clarity and focus. Being “fearless” is not a good thing. (Without fear, you’d be incapable of assessing or avoiding risk.) As Mark Twain said, “Courage is resistance to fear, mastery of fear, not absence of fear.”

Will it ever feel easier?

Obviously, you’ll get a different answer from every entrepreneur you ask, but this is my experience: It doesn’t get easier, but you become more resilient. There will always be waves of difficulties that feel insurmountable and new, but the longer you stick with it, the more experience you’ll have getting over some kind of wave, and you’ll be able to trust — to some extent, anyway — in your ability to at least weather the storms, if not ride the crests.

This doesn’t mean you won’t feel, at least once every year, like you’ve failed utterly and it’s time to throw in the towel. (Again, this is my experience, and maybe not everyone’s.)

It also doesn’t mean that life as an entrepreneur is a non-stop storm of crazy proportions. There are ebbs and flows. There have been times when I felt entirely confident about how things were going. Those were the easier times that I think you’re holding out hope for. They do exist.

But I don’t want to tell you that it ever feels like that forever, or like there’s some kind of goalpost beyond which you no longer encounter dark nights of the soul.

As a friend of mine once put it, “At the end of the day, life is just the death and resurrection show.” There will be moments of intense sweetness and light. And there will be darkness. The only thing we can count on for sure is that it’s all transient, i.e. this too shall pass.

I hope this isn’t too dark. I don’t want to sugar-coat things just to cheer you up. I also don’t want you to feel alone.

Failure is Not the Whole Story.

And here’s what I really hope you don’t feel: that if you close the doors on your business, that means it was a failure.

I don’t know if that’s going through your head, but again, this is my experience. Any time I faced the possibility of closing down my business, I felt like doing so would mean admitting failure. And if I could go back in time and talk to that younger self, I would say: look, you do what you need to do to get through to the other side of this. That’s not failure. That’s survival. That’s reinvention. That’s creative problem-solving. And if the business has to close down now, so be it. It had many successes, and its ending does not define its impact — or yours.

I’m not trying to put a feel-good spin on failure in the pat way that Silicon Valley bros talk jauntily about “failing up” and “failing fast” and “I’m super privileged so I can afford to ‘fail’ and then blog about it to prove how cool I am with failure.” Failure is awful. It’s really, really hard. Closing the doors to your business would feel like failure, and yet —that’s only part of the story.

Calling it “failure” carries with it a strong suggestion that you have failed. That you could have done something to fix it. My hope is that you not feel defeated, or like you’re doing something wrong. There are way too many variables in this game to pinpoint any one thing that could be causing your business to falter.

Welcome Your Tears.

Finally, if you find yourself crying: that means you’re letting go of something that needs to be released.

Now’s a good time to ask yourself what that thing is, and how you can help it move along.

It might be a dream. It might be an image of yourself. It might be a relationship (or several).

Let it go, let it go, let it go.

I can’t promise you what the future holds for your business, but I can promise you this: pushing the fear away will only guarantee it will come back with a vengeance. Asking it in, and letting it show you what you need to attend to, will allow you to take your next step with wisdom and integrity.

Love and courage,

This post was originally published on Medium.