Manageable Guides

Expert views on topics relevant to all leaders and teams.

Simon Devonshire is a serial entrepreneur, investor, NED and chair. He has worked in very big corporates like O2 and for start-ups. His career has given him the chance to observe the repeat behaviours common to successful entrepreneurs and leaders. In this guide, he shares some of these observations, with an emphasis on knowing when to stop.

Hello, I'm Simon Devonshire. I'm a serial entrepreneur, investor, non-exec director and chair, and I work across a portfolio of different businesses from very large corporates through to innovative ventures. So, I've had the luxury of a really privileged career in that I guess what makes that career unusual is the extent to which I've worked in both very big corporations and run big corporations, as well as also starting early stage ventures and helping grow startups. The last few decades have given me a unique perspective from which to observe the repeat behaviours common to successful entrepreneurs. What I'm trying to do is to codify and distil the learnings and lessons and observations from that, in an original way to help give really practical insights for people in business, to help them flourish and be successful. There is a lot of conversation about startups, starting up, the obstacles and challenges of creating a startup, and what to do with a startup when you've got one. But actually, perhaps not enough conversation is taking place about the challenges and the stresses and anxiety caused by knowing when to stop. I think that stopping is relevant to all people in businesses, whether or not you've got a startup or whether or not you're working in a very big corporate. The challenge is, knowing when it's appropriate to stop. I'm Simon Devonshire, and this is my Manageable Guide to know when to stop.

So from the perspective of an entrepreneur, what I've observed is that there are five dilemmas, five conundrums that cause entrepreneurs and business leaders to get stuck, and the common denominator of those dilemmas is the issue of stopping. Very briefly, I will run through those five different conundrums. So the first one is persistence. When I started the journey, I thought, specifically, the attribute and characteristic most important for business success was resilience. And over time, I've changed my view of that and now I believe that persistence is singularly the most important attribute. I've learned that if you have enough goes at something, the likelihood is you can eventually find a way of making it succeed, but then the challenge that that raises is, well, when do you know when to stop, when to call it a day? When's enough, enough? So number one is persistence.

Number two is discretionary effort. Increasingly, businesses are dependent on their team, at all levels going above and beyond the call of duty, of going the extra mile and investing their discretionary effort. But the danger that creates is one of burnout and increasingly, as we come out of post-pandemic, what I'm seeing is more and more cases of acute fatigue and exhaustion. So knowing when to stop is vitally important.

Competition. Competition is a really important thing. Often in venturing there is an establishment amongst investors that if you can't name your competitor, then perhaps your market doesn't exist. So what if you're pioneering something completely new and there isn't competition? How do you know whether or not you should go further? You know, how do you know whether or not you should just stop? What if customers don't get your proposition? Is that the time to stop? And actually, it's often increasingly very difficult for customers to evaluate new innovation, new technology. So when is it appropriate to pursue an innovation and when should you stop?

Then finally, I have this mantra about don't be the first or or don't necessarily aim to be the best. The best can be just a shortcut to becoming the most expensive. What I try to really encourage businesses to think about and everybody that works in a business at all levels is how to be better. Next is customer centricity. So how and why is your proposition better than the alternatives, particularly better than the option of doing nothing? But then the challenge is, well, when is good, good enough? When do you start? And in a lot of businesses, both large and small in a lot of different layers of management, the temptation to overly finesse a product or proposition, to overly work on it, to set an unrealistic expectation within your customer group, that then becomes very difficult to deliver against them to fulfil.

So those are the five persistence, discretionary effort, competition, customer centricity and being better. And in all cases, the common denominator is knowing when to stop. So if I think about how best to distil that into a practical guide, into a Manageable Guide, the first one is identifying the point at which you should really meaningfully take stock and decide whether or not to stop, to pivot change course and direction to evolve, iterate, or whether or not, to literally cease what you're doing. Typically, the evidence would be things like fatigue and exhaustion, people falling out of love with what they're doing. And for me, the issue that you really need to tune into is conviction, when you start to lose heart, and when you start to lose genuine interest in what it is you're doing. And the reason for that, and why that's so very important is that in business, I've yet to find a challenge or obstacle that isn't surmountable, that can't be resolved when broken down sufficiently.

So business is not like deep science in which I also work where genuinely, we're trying to move some very difficult things forward that have not been achieved previously. In business, things are much more simple and straightforward. You may have an issue with your supply chain, you may have an issue with staff retention, you may have an issue with customer loyalty, you may have an issue with getting more sales. However, in most cases, my experience is all of those are solvable and broken down enough. So, the time to really think about stopping is when you no longer are compelled to confront those issues, when you really are not motivated by them, those challenges were new, when your heart is no longer in it, when you fail to seek external advice. One of the things that is so important to business success is your ability to get input from other people. So I think at all levels of management, that one of the key things to look for is that notion of genuine exhaustion. And my sort of soundbite on that is that haggard is not a good look in a lot of businesses.

And I think there's a couple of things that are really important. So the first one is, lead by example. So know when to take a break yourself. If you work really late, if you send emails in unsociable hours, whether that's in the evening or at weekends, you're actually creating that behaviour amongst your team, and you're infecting your team with that as an expectation. So I think you know be very careful of your own management, of your own time, of your own performance. That would be the first thing. In terms of taking a break, I believe that success in business is fundamentally ingrained in animal instincts and the good news is that we are born with them. One of the animal instincts that I think is particularly relevant here is the notion of hibernation, of knowing when you need to go and rejuvenate. The other thing to recognise is that the appointment and hiring of new talent and staff can really be disproportionately rejuvenating. They bring with them a fresh perspective, but they also bring with them renewed energy, and it's not to be underestimated. It can be kind of equivalent to calling the cavalry.

The second point really is how to navigate that path. So I've given five scenarios in which stopping is sort of fundamentally the common denominator. But what that doesn't tell you is how to navigate them. And I think that there are some common pathways that help in all five of those situations despite their difference and fundamental to that is the competency of validation Specifically, to evidence, the best way forward, whether that's for you, for your team, or for your customers. And validation comes in many different forms. So the ultimate form of validation in business is of course sales. Can you compel people to part with their hard own money in order to buy your product or service? That's the ultimate form of validation. But there are many other forms of validation that are equally applicable to all businesses, both large and small.

One of them is investment. Can you compel people to invest in your business, whether that's to buy equity in your business or to fund it or to lend money to your business? Another form of validation is talent acquisition and whether or not you're able to hire people to come and work with you to join your team and to join you on the mission that you're on. I think that's relevant to all businesses, both large and small. Validation comes in many forms. But fundamentally, what you're looking for is evidence that people are wanting to engage, to buy the product and service that your business offers. The mistake that people often fall into is creating products and services in their own image that because they find what they're doing compelling, that others will share that compulsion. That's not necessarily true, and I'm greatly worried by the notion of build it and they will come.

My experience is build it, and they won't come. And so validation is all about making sure that what you're doing is actually compelling to the people that you're trying to influence. So I think, in this Manageable Guide, we've tried to cover a lot of ground in looking at common scenarios and business at all levels of business, both small businesses and large businesses where the issue is knowing when to stop. Whether that's simply that the business isn't working, or that you're not sure whether or not your proposition is compelling. Whether or not you're overworking and whether or not you're comparing your team to overwork. I think the key takeouts and the practical things to look for would be for instance, looking for genuine signs of fatigue, to avoid exhaustion, looking after yourself and your team, and to really tune into validation. Also, whether or not the market is compelled by the proposition that you're putting forward to not overwork, to manage your customers expectation, to use technology to your advantage and to use technology to enhance your productivity. I think finally, to really tune into this notion of conviction, because I really genuinely believe in persistence, that if you have enough goes at something and you iterate and evolve, you can crack anything. The time to stop is when you just don't have the energy, capacity, resources and you're not getting the external input to be able to do that one more go and it's all about the one more go. I'm Simon Devonshire and this is my Manageable Guide to knowing when to stop.