Collaboration is a must-have skill, but how do you collaborate with someone you don't really know?


The word together to represent collaborating with other people
Photo by Nick Fewings on Unsplash

Like it or not, collaboration is critical in business - it can be a force multiplier, providing leverage and scale where one person or one group alone does not have the skills, knowledge or capacity to deliver a project or solve a complex problem.


If you are a leader or aspire to be one, then collaboration matters. It isn't always easy for busy, driven and successful people to collaborate. Often the tendency is to think in either/or terms, as in win/lose, rather than working together to achieve win/win outcomes. Even though organisations might say they value teamwork and collaboration, the incentives at work often say something entirely different - be it the performance-related bonus or scarce promotion slots. It is the ability to work against, not with, this cultural reality through short and long term collaborations that lead to career and business success.


"To achieve your goals, it matters less how smart you are or how much innate talent you're born with. These things are important, but they mean little if you don't understand one thing. You can't get there alone. In fact, you can't get very far at all."

- Keith Ferrazzi



Almost all the work you will do is through relationships with people. Whether those people are within your organisation or outside, the ability to collaborate effectively is critical. Unsuccessful collaborations will delay projects, introducing inefficiencies, cost over-runs, wasted time and effort, missed opportunities, damaged relationships, and inevitably increased conflict.


The reality is that more and more of us have to work with different people, often people we don't know very well, to get our work done. Collaborating is how an increasing number of us work today in the 24/7 super fast-paced globalised business world. Collaborating across boundaries of all kinds: expertise, language, distance - you name it - to get work done and achieve the desired goal.


  • Freelancers or entrepreneurs looking to collaborate with like-minded people or service providers to deliver a large project that would be impossible alone.

  • Transformation initiatives and project teams within large organisations that need expertise from several different cross-functional departments.

  • Leads and partners of consulting teams when selecting the people to give their clients the best chance of a satisfactory outcome.


We need to ensure that our collaborative enterprises have the very best chance of success. This is especially needed for work that is complex and unpredictable and for solving big problems. An often-overlooked element that I have found crucial for success when reviewing the collaborations I have undertaken over the past five years is the choice right at the beginning as to whom to collaborate with. That's right, we often have a choice, and so it is better to be prepared to give us the best chance of choosing the very best people and organisations with whom to partner.

How do you choose whom to collaborate with?

And just as importantly, should you press ahead with that collaboration?


You get to decide whom you're going to work with, whom you will partner with, the best people to collaborate with. Especially relevant for knowledge workers whether you are an independent freelancer, entrepreneur, or small established business. Whether building a team, for associate work, affiliating with others, hiring people, or selecting a service provider


You may not think you have a choice with whom you get to work with but bear with me, and I will explain how a guiding framework like this will help you with hiring and whom to collaborate with. Getting better at selecting whom to collaborate with will also strengthen your decision-making when pursuing new opportunities and ending existing ones. Otherwise, it is common to launch ourselves into many projects to create multiple streams of income, opportunities to work with new people or take on additional responsibilities to impress those senior to us. For most people, it just bogs them down, and nothing flourishes.


As Derek Sivers says, "We're all busy. We've all taken on too much." So any collaborations should be a "HELL YEAH! Or No.", not a meek yes.


I want to share my learnings from the many collaboration opportunities I have had with some fantastic people and organisations over the past several years. Some are still ongoing, others came to a natural end, others have not been successful, and several I said no to. During this period, I have curated a guiding framework to help me decide whether to invest further, refined by the successes and failures.

Key questions to answer before entering into a business arrangement


When it comes to whom you work with, you often have a choice, and hence it is essential to make well thought out (conscious) decisions, rather than simply going with the flow because it feels easy at the time. What follows is an overarching framework - keep it in mind, there will always be exceptions. I have learned there are a few key questions to answer if you want to enter into successful business collaborations, beginning with questions about yourself:

First, help others get to know you better.


Learning how best to work with others is a considerable challenge that often derails teams, projects and business collaborations. Over the years, I have witnessed and experienced talented individuals struggle because of misunderstandings, poor communication, and conflict left unchallenged. Failure to communicate clearly causes many of the issues within today's workplaces.


Writing and sharing a user manual, also called a "working with me manual", will improve communication, help set clear expectations, and share the best ways to interact and get the best work out of you. Let's remove the guesswork, which will aid with establishing trust and increasing the bonding of the people you work with, to each other, and the common goals. Find out more in this article.



7 questions to ask

Align yourself with a business or person who shares similar goals - don't assume that you know the other party's values. Take time to articulate your shared vision and make sure that you're on the same page.


  1. What is our shared purpose?

  2. How much time and energy can each of us commit to the project?

  3. Can we test the collaboration first - can we conduct a low-risk experiment to test the waters before getting into a more serious commitment?

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

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

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

  7. How will we review progress and give each other feedback?


Questions to delve in deeper


Getting into the details, view this as the next level. The following questions are written for coaches who want to assess collaboration opportunities with other coaches. Feel free to alter to better fit your particular situation and need.


Given that we will each need to invest a lot of time together - here are eight further questions for me to consider and help me decide whether I want to continue my involvement or to opt-out:


The scale of 1 (very low) to 10 (very high)

1 - Where do I rank my time and investment with this group compared to my other work priorities?

2 - Will I be happy to share my existing clients with this group?

3 - Will I be happy that some members will bring in considerably less business than others to the group, but they have other strengths that more than make up for that?

4 - How do I feel about making this group my primary commitment to coaching?

5 - Am I comfortable recommending the other coaches to my clients?

6 - Will I be happy to turn up to a client with anyone from the group?

7 - Do I see value from being a member of this group for:

  • The opportunity to coach each other?

  • It to be a support group?

  • It to be a source of learning for me?

  • It to be an enjoyable place to spend my time?

8 - Do I firmly believe that being in a group is important to land interesting work that I could not achieve solo and that work is consistent with my financial aims?


The aggregate average score should be above >= 8 for a "HELL YEAH!" collaboration opportunity.



I am confident that this way of looking at whom to collaborate with will give you new and helpful leverage both personally and professionally - leverage to approach opportunities differently and solve problems that you didn't realise you had.


Fewer, better curated, more selective collaborations and partnerships


"If you want to go fast, go alone.
If you want to go far, go together."

- African Proverb

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