Essential Entrepreneurial Enabler: Herding Cats

Driving forward in a startup almost always comes down to herding the relevant cats into alignment to achieve the goal at hand.  Herding cats requires an essential blend of skills – and the results can be quite value-creating.

Startups may need technology, funding, intellectual property, customers, and suppliers, but at the most abstract level, startups are constructed out of one fundamental building block:  people.  Everything else fuels the people, equips the people, convinces the people, aligns the people, and leverages the people. No matter what you are trying to do, you will almost always need to engage with other people to do the thing at hand. That means that a startup leader’s ability to lead people is an essential entrepreneurial enabler.

For me, a metaphor that captures the challenges of accomplishing things via people is the idea of “herding cats.”  Why cats?  I think of cats as strong, curious, active, powerful, capable, intentional, and independent beings who have their own opinions, motivations, and interests.  Unlike dogs who are endlessly interested in their owners and eager to engage in whatever game might be on offer, cats sometimes want to get close and engage – and sometimes they simply go their own way.  Persuading a group of cats to engage with each other and align (aka ‘herding’) is tricky and takes persistence and creativity.  And yet, achieving alignment to achieve a series of interlocking goals is an excellent description of the essence of a startup journey!

So, when herding “cats,” first you must know your direction and purpose.  What is the point of herding aimlessly about in circles?  Figuring out the next elements of your plan for success – what you need to accomplish and who needs to be on board in what way to achieve that element is the first step in successfully herding.  Know what is essential and where you need to go.  The more clarity you have on your target, the easier it will be to work towards aligning others with the desired path.

Second, when herding “cats,” you need to know your “cats.”  Like “cats,” people are similarly complex and variable. Think of it this way (please remember these are analogies intended to get you thinking, no insults intended!) – dogs and horses are usually pretty predictable.  If you throw an attractive toy, the dog will almost always hare off to try to get it.  As prey animals, horses assume everything is a threat, and the right answer to a threat is running. If you can keep this in mind, you can usually persuade horses to go the way you want them to.  On the other hand, cats are much more complex to work with. They are independent thinkers, often with mysterious needs and goals of their own. Just like people. 

So, the key to success in figuring out how to herd a group of people in the direction you are trying to drive in is getting to know each individual, each team, and each organization. Assuming that there are differences is a good place to start because it puts you in a humble, learning frame of mind.  As you go along and get to know the relevant people who are important to your project, seek to get to know individuals by paying attention to what you can learn about each person’s motivations, patterns, communication style preferences, capabilities. When I meet and begin investing in building a relationship with someone in a business context, I pay attention to tiny signals about how they prefer to communicate.  I notice how they sign their emails and reflect that back when I respond.  I notice if they need reinforcement from a leader to react or if they are proactive on their own.  I look for hints of what they think is important and what their motivations are.  By being sensitive and aware, I can begin to understand how to align their needs and goals with my intended path – and communicate my care and respect for them as I ask for their help.  Then I have a much better chance of finding a win-win dynamic to encourage them to willingly join into the path I am constructing.

Of course, it is rarely as simple as a one-to-one relationship. Accomplishing a startup’s big goals almost always involves aligning multiple people in complex ways to navigate a winding road. Determining who needs to be involved and why is a critical component. Essentially, what colors of cats do you need?  This can be a question of skills, temperaments, roles, organizational affiliations, current responsibilities, and any number of other dimensions. Think about the goal and be creative in thinking about who might be needed to help you get there.  For example, getting a new product implemented at a large customer organization may require the help of many functions on your startup team as well as possibly on the team of a partner organization plus an executive sponsor, administrators, technical team members, and front line users at the customer organization. Sorting through who is needed to do what and how they all relate to each other is often a complicated and uncertain process, a process you must navigate imperfectly with many gaps in the information you wish you had and uncertainty about how all the pieces might come together. The process will almost always be an evolutionary journey as you discover new people who need to be brought into alignment with the ones you already know about.

As you progress and your group grows, it increases the complexity of the herding process, and you run the risk of losing sight of all the interlocking pieces of the puzzle you are assembling. By continually driving clarity on the big picture of what is needed and what your goals are – as well as constantly learning and discovering what your cats’ goals and needs are, you can keep creating an ever more complex map and keep searching for those situations where overlap might enable win-win-win-win solutions and great alignment that draws the cats down the road.

As you herd your ever-growing group of cats, the communication demands become greater. You will need to learn the right communication cadence that maintains focus, momentum, and respect without being annoying or overwhelming. Similarly, as you are busting down barriers, you will need to finesse questions of who to touch about what, how to navigate the landscape of different peoples’ roles and responsibilities, and when and how to escalate.  Tools like giving appreciation and credit, being swift and responsive, making others look good to those that matter in their world, and treating all of the many cats with great respect as you make it easy for them to do what you want will help encourage your cats to journey along with you.

At the end of the day, herding cats is an essential skill required to get disparate people aligned and accomplishing great things. Those who want to opt out of the people navigation skills required will find their projects struggling. Superb leaders and project managers become adept at figuring out how to bring diverse groups of people into alignment and motivate them to accomplish goal after goal after goal, for that is how startup value is created.