Why outsiders make the best entrepreneurs

Snip20151128_2This article first appeared on the entrepreneurs’ news-source website minutehack.

Outsiders and misfits have the wrong traits for the formal economy, but can make excellent entrepreneurs. Yet there are dangers to avoid. By Robert Kelsey

First let’s nail the outsider. We’re those within a tribe but not of it. Uncomfortable in our own skin, we’re socially awkward – loners in the crowd or even the changelings within our own family. For whatever reason, we simply don’t fit in: we’re the unclubbables, the misfits – the ones rejected by or rejecting the colony.

At first glance, such an outlook seems unconducive for success. In fact, it looks like a disaster, not least because traits can include problems with authority, distorted empathy (in which we root for the bad guys), sensitivity, cynicism, anger and even imposter syndrome (in which we assume ourselves incapable of the role we hold).

Even at second glance, such traits are a struggle for anyone trying to navigate their way in the formal economy. Major employers are all hierarchies: something outsiders – as individualists – instinctively dislike. Too often the result for outsiders is failure, which compounds their sense of isolation and alienation. We develop a gnawing sense of marginalisation: of somehow missing out on the party everyone else is invited to. Extremism can follow, even criminality.

And yet the very traits that make outsiders so incapable of success within normal educational and occupational structures is exactly what’s required for entrepreneurship. Unleashed, outsiders can change the world – as outsider entrepreneurs such as Steve Jobs, Mark Zuckerberg, Howard Schultz, Oprah Winfrey and James Dyson have shown. Indeed, those traits can be turned around and presented as the very things entrepreneurs need for success:

Innovation. It’s a cliché that entrepreneurs are all innovators – many simply want to work for themselves. But it tends to be true that it’s the innovators that strike it big. They have a thirst for doing things differently, for taking concepts to the next stage.

Contrarian. Such innovation, for entrepreneurs, is often the result of a stubborn bloody-mindedness that sets them against the crowd. While most people are happy to coalesce in groupthink – and allow it to dictate their entire lives – outsiders tend to do the opposite (hence the distorted empathy). And if there’s one defining trait for a successful entrepreneur, it’s that they instinctively swim against the tide.

Creativity. Outsiders tend to be highly creative (a cause and effect of their childhood isolation), which is, of course, a major requirement for entrepreneurship – in fact, another defining characteristic. Certainly, creativity can help entrepreneurial offerings stand out from the crowd.

Individualism. If outsiders are any one thing, they are individualists. Sure, many become revolutionaries railing against what they see as a venal and exploitative economic system. But just as many see free enterprise as the very structure that liberates them from the need to conform. They simply need to find a way of making their individualism profitable.

Courage. As with successful entrepreneurs, successful outsiders possess bravery in buckets. Sure, it can come across as bravado – even recklessness – but it’s actually a willingness to take risks: a valour born from the frustrations of their tribal positioning. Indeed, if there’s a defining characteristic between successful outsiders and those that remain alienated and frustrated – its pure guts.

Not all good news

Such a close alignment between the outsider and the entrepreneur offers enormous hope to the not-insignificant proportion of the population leaving full-time education thinking that they don’t belong: usually because that’s what our overly-structured and linear education system has taught them. Yet it’s not all good news. The very traits that make outsiders suitable entrepreneurs, can lend themselves to problems further down the line.

For instance, outsiders tend to make poor managers. While able to forge their own path through creativity, determination and bravery, outsiders are essentially selfish people, which makes most successful outsiders egotists. The needs of their team are rarely considered, which – over time – can hinder their growth. So entrepreneurial outsiders need to develop managerial skills, or quickly employ someone with the sense of community, empathy and nurturing they lack.

Potentially more detrimental, however, is the outsider’s poor judgement. Our youthful alienation has rendered us incapable of making strong decisions based on meeting positive and planned future objectives. Instead, we tend towards emotional decision-making focused on our immediate, usually negative, needs – often to do with avoiding triggered fears or insecurities. Of course, much of the advice here concerns removing our emotions when making decisions, which – for outsiders – is impossible. Better to include it, but only as an equal to more positive evaluations.

And the final flaw for outsider entrepreneurs is a propensity towards sociopathy. According to Martha Stout, author of The Sociopath Next Door (2005), sociopaths have “no feelings of guilt or remorse no matter what you do, no limiting sense of concern for the well-being of strangers, friends, or even family members”.

Sociopaths are pathological liars and manipulators. They can be charming and even appear as empathetic team players, when they are anything but. Yet the real problem for entrepreneurial outsiders is not that sociopathic tendencies result in failure – on the contrary they can lead to spectacular success. It’s that they have no limits: eventually, the sociopath – admittedly after a period of seemingly-stupendous achievement – will overreach themselves.

Of course, when the inevitable crash comes, their numerous enemies will be happy to put the boot in. That said, constructive sociopathy can work wonders. Here, entrepreneurial outsiders set positive and constructive goals (“getting rich” being a negative goal based on overcoming our insecurities) that help entrepreneurs make better decisions that build better companies.

And, no, that doesn’t mean we’ll end up as insiders.


Robert Kelsey is author of The Outside Edge, How Outsiders Can Succeed in a World Made by Insiders, published by Capstone priced £9.99

He is also deputy chairman of the Centre for Entrepreneurs.

Q&A: Making good first steps with your career


Below is an edited transcript of my live Q&A with the National Centre for Universities and Business, a not-for-profit organisation bringing together universities and business.

Adi Gaskell (moderator): Hello all and welcome to this live Q&A – Making Good First Steps With Your Career – with author Robert Kelsey. Robert is the author of four books on how to succeed at work, and is co-founder and deputy chairman of a leading entrepreneurs’ think tank: The Centre for Entrepreneurs. So let’s get started:

Comment From David: With the web I really struggle with information overload. How can I overcome this?

Robert Kelsey: Hi David, In my view this is similar to decision-making paralysis or poor judgement, in that we can have too much information to make a decision or judgement, not too little. Yet I think this comes from poor goal-setting. If you have a detailed long-term goal with a worked-through plan and strategy for achieving it you are no longer receiving information, you are seeking it. At this point only the right information matters but, crucially, you can determine what constitutes the right information. There’s something called the Reticular Activating System in which the brain alerts you to what’s of interest. For instance, my son loves football and can spot a Chelsea or Arsenal badge (perhaps in a shop window) from 100 metres. Once you know what you’re looking for, in other words, that’s what you’ll focus on.

Comment from Joanne: I feel like I’m stuck in my job but don’t really want to jump ship to move on. What can I do?

Robert Kelsey: Hi Joanne, I guess you need to think about your long term goals. If you take a 10-year view about who you want to be and where, you can then add some milestones for five, two and one years and even six months, three months etc. Remember you only need to worry about what HAS to be in place to meet the later goal – so what MUST be achieved by year one to meet the two-year milestone etc (after all, you have 10 years to get to where you want to go). Creating that path will give you clarity of thinking – and should help motivate you to act. Indeed, you may well find that what’s needed is a new role in the same place, or one more year getting experience where you are. But it might also make you think – “enough! Time to move on”, although you should now have an idea of where to look.

Adi Gaskell: That’s a really interesting point Robert. Do you have any good sources for help in taking this kind of long-term thinking?

Robert Kelsey: Visualisation is a strong technique, though one that has been criticised lately for creating false hopes (nonsense in my view!). By visualisation, I mean simply putting yourself in a dark room, closing your eyes and projecting yourself 10 years forward – and be very detailed.

Comment From John: I’m worried that my career might be automated, what would you suggest I do?

Robert Kelsey: This is a concern for many people in many industries. However, I would differentiate between a job and a career. Jobs will certainly be automated. But will careers? Careers usually follow a pattern that starts with learning/training, before going on to execution, then management, then innovation, then ownership and then regulation/control. Automation is simply a change at the execution phase of a career, which is where people start. Management will not go away and nor will innovation, ownership or regulation. So – if this is your chosen long-term career (something that motivates you wholeheartedly) – remain flexible and be open to new skills and learning (yes, including those involving technology). And quickly show your management skills. That way you should stay relevant as your industry changes around you.

Adi Gaskell: It sounds like the concept of lifelong learning is more important than ever before. It’s something I feel that Anna is interested in with our next question.

Comment From Anna: If you were a student today, what would you study?

Robert Kelsey: That’s a tough one. I often think economics would be a great subject and then of course there’s psychology. That said, I enjoy the fact my research has led me to discover the right psychologists for me: as I’ve tried to deal with my personal issues (and then write about that path to discovery). So I guess my old course of politics and modern history did give me a broad perspective….and I enjoy using it.

Adi Gaskell: It sounds very much like a broad skillset is valuable in allowing you to adapt to any changes that occur. Would you say that’s fair?

Robert Kelsey: It’s fair to a point. The trouble is that the world is so specialised that we do need to discriminate in terms of what we want to do. That said, with long term goals in place we can develop the skills we need over time. People are simply too addicted to instant gratification and that, these days, includes careers. It’s great to be impatient and it even works to be a little frustrated (highly motivational). But everything involves an apprenticeship. You can’t cut corners in this respect.

Comment From Liz: I often see that we need personal “brands” but I don’t feel comfortable promoting myself. Do you have any tips?

Robert Kelsey: Hi Liz, You put quote marks around “brands” when I’d correct that to encompass “personal” so its “personal brands”. That means this is YOUR brand, for YOU. It doesn’t have to be any more public than you want it to be. By setting long-term goals you are deciding what sort of person you want to be. This may change over time and room for adjustment is needed. But goals are there to establish some principles and get you going. And that involves calculating your preferred future self, which is a holistic quest inevitably involving an element of public perception. So who do you want to be? And how do you become that person? This is 90% internal, but it will inevitably involve external elements – not necessarily in terms of self promotion but, for instance, in how you dress or hold yourself, or even speak. It’s all part of Brand Liz.

Adi Gaskell: Excellent stuff, hopefully useful advice for you Liz. We have a fresh question coming in from Andy about that prickly topic of failure.

Comment From Andy: There is a lot written about failure being good, but it doesn’t feel like that in my workplace. Is it possible to overcome this as a (lowly) individual?

Robert Kelsey: Hi Andy, Undoubtedly, failure can be painful and disabling. It can undermine our confidence and sap our will to continue. And, yes, many organisations have an intolerance of failure that can generate a paralysing fear of failure. Can anything be done, especially as a junior? Well, first ensure that you have your own goals that are independent of the organisation you work for. They are the goals by which to measure yourself, not those imposed by others. They should be long-term, detailed and all-encompassing. Second, realise that – with respect to these goals – any setbacks are simply feedback moments, requiring you to learn the lessons, adjust, and carry on. And by carrying on you’ll soon outgrow any organisation that has an intolerance for innovation simply because it cannot accept failure. So it could just be that your attitude to failure is ahead of your employer’s: in which case you need to find an employer with a more enlightened view (or stay and try and, slowly, convert them to your way of thinking).

Comment From Andy: I suppose the “innovators” lot is always going to be a tough one. I’ll keep plugging away. Thanks for your detailed response Robert

Adi Gaskell: Superb answer Robert. This topic of failure feeds into our next question from Joe around the kind of expectations we have when entering the workplace

Comment From Joe: I haven’t entered the workforce yet, but a lot of my friends are disillusioned already. Is a dream career unrealistic?

Robert Kelsey: Hi Joe, Unrealistic by what timeframe? You need to set strong goals but also give yourself time to achieve them. Notice something about authors, TV presenters, actors, entrepreneurs etc – most of them are at least in their 30s if not 40s and 50s. What they had, however, is strong goals and a worked-out path for achievement. They also had resilience so were able to use setbacks as feedback moments. Also, with strong goals you feel something of the feeling of achievement just knowing you are on the right path.

Adi Gaskell: It takes a long time to become an overnight sensation :). Autonomy is often billed as one of the most motivational aspects of modern work, and Chris has an interesting question about this in relation to “intrapreneurship”.

Comment From Chris: Can you be an entrepreneur from within an organisation?

Robert Kelsey: Hi Chris, It’s tougher – that’s for sure. No matter what organisations say, most want you to – primarily – toe the line. But the answer is still yes, but cautiously. You need to establish yourself as a “trusted advisor” to seniors first – by understanding the organisation and helping it achieve its goals. Only then will you have won the right to a hearing. And at that point, anything is possible. Also, as your career progresses the more entrepreneurial you will have to be – helping organisations add value, not simply executing others’ plans.

Also, coming back to Adi on autonomy – yes it is motivational but autonomy also comes from within. If you are pursuing your own goals over the long term, then one cranky boss making you stay late isn’t going to worry you too much. You know where you’re going and you’ll know whether this organisation is right for helping you along that path.

Comment From Chris: Makes sense Robert. Get some money in the bank first. Thanks.

Adi Gaskell: That’s an excellent point about earning the trust of your employer. We have another question here from Daniel that is along similar lines, but this time on earning trust before you even join.

Comment From Daniel: Is an internship a good thing to do?

Robert Kelsey: Hi Daniel, It depends. At Moorgate (my PR firm) we, instead, take people on full time but for a trial period, so they are properly paid and properly part of the team. Around 75% make it through the trial to become an Account Exec. I see too many CVs with the odd week here or there making the tea (usually for a family friend), so – as an employer – I’m a sceptic. Yet if the training is real – involving developing skills towards what you want to achieve, then great. But as a system, I think it a little unfair – and I think that’s being increasingly recognised. Tip: pitch smaller employers but in the right field – someone without the fat to abandon you to making the tea. They’ll throw you right in the deep end and you’ll get real skills/experience.

Wayne Ellis via Twitter: Are we finally in the “free agent nation” that Dan Pink predicted a decade ago?

Robert Kelsey: Hi Wayne, We’re getting there. But I do think people need to think about skills and experience, as well as freedom. If you know that freedom is coming – that you can become a freelancer or start your own business – then you simply need to develop the right skills for that goal, which could involve a period with an employer (a personal apprenticeship, if you like). Another aspect to this is scale. By staying in a company – for say five years – the scale of what you can achieve beyond it may be that much larger. I had a friend start a business straight after college – he was dealing with micro businesses and small traders. You know what – he still is. Whereas those that started a business later – once they’d learnt to deal with C-suite executives – started businesses further up the foodchain. Worth noting.

Adi Gaskell: Super answer Robert. I appreciate we’re running close to time so I’ll rattle on with the next question, this time from Jess

Comment From Jess: I’m setting myself up for a radical career change into business administration, what should I be concious of to avoid stalling and to help identify fast-tracking opportunities within the new career?

Robert Kelsey: Hi Jess, The biggest thing you need is a career path – but one you create yourself. So calculate what that path looks like over the next 10 years and make sure you stay on it (though with some flexibility, of course). What I like about this is that it gives you judgement and helps with your decision making. If it’s on the path – it’s a yes etc. Of course, things don’t always go to plan but, even here, you will be able to tell what’s on and off the path. And of course you can always set that 10 year path every year, so you are always 10 years from achieving your ultimate goal (though making very strong progress in the meantime).

Wayne Ellis via Twitter: Robert Kelsey: we need to think about skills and experience: good advice.

Adi Gaskell: Sage advice Robert, start at the end and work backwards. We have just about enough time to squeeze one more question in from Adam on starting a business with student debt

Comment From Adam: I don’t feel I can start a business with so much student debt. Is it possible?

Robert Kelsey: Hi Adam, Then don’t start a business yet. Why not start a business in five years but go and work for someone now that will give you the skills you require? I always say that there is no harm, at your stage, in letting other people pay for your mistakes. By that I simply mean that, if you were running your own business and making the inevitable learning errors, they could harm your future prospects (though you can always recover). So why not see job one as the apprenticeship for running your own business? It’s a great goal – strengthened not lost by some experience in the workplace, which also means you’ll be earning and paying down that debt. Hope that helps!

Adi Gaskell: Super advice Robert. Ok, I think that’s about all we have time for. I’m sure Robert’s fingers must be about to fall off. Don’t forget that Robert has recently published an excellent new book called The Outside Edge. If you would like to buy a copy, if you use ‘VBM41′ as the discount code you can receive a 30% discount. I’d like to thank everyone for participating in what has been a fascinating hour, and most of all to Robert for giving us his time and insights today.

Robert Kelsey: It’s been a pleasure – happy to take more questions via Twitter @robertkelseywsy



The 10 Best Books for Entrepreneurs


This article appeared in The Sunday Times supplement The Start-up List 2015

Robert Kelsey picks his top 10 entrepreneurial reads.

  • The E-Myth Revisited, Michael Gerber. The original exploder of entrepreneurial myths (swashbucklers we ain’t), this revised edition should be compulsory reading for anyone thinking of going it alone. Gerber’s dispassionate examination of “why most small businesses don’t work” can certainly help would-be entrepreneurs avoid the same old mistakes, traps and false assumptions.


  • Worthless, Impossible and Stupid, Daniel Isenberg. More myth-busting about the nature of entrepreneurs. We don’t have to be innovators, experts, lucky, clever or young, says Isenberg. Yet he’s keen to plant some fables of his own – including our “surprisingly ubiquitous relationship with adversity”. We’re contrarians, he says, seeing value where others don’t. And we persist, long after the sane have surrendered.


  • The Entrepreneur Revolution, Daniel Priestley. While Priestley’s global philosophy borders on the cheesy, his radical proselytising about the changed nature of work gives way to some seriously clever ideas on how to discover – and reconcile – your place in the entrepreneurial landscape. His Ascending Transaction Model transformed my approach to marketing and his Create Vs Consume dichotomy is the clearest indicator of your true taste for entrepreneurship.


  • How to Get Rich, Felix Dennis. Business bookshelves groan with “how I made it” entrepreneurial tales of derring-do. Yet none quite match this one in terms of both chutzpah and bluntness. Dennis’s zany madness somehow gets to the point, meaning that – as a collection of biographical anecdotes – it’s probably the most relevant (as the title implies). Judicious salt-pinching required, and try not to be put off by the poetry.


  • The Beermat Entrepreneur, Mike Southon/Chris West. Feels in need of an update, but the first book to offer solid practical advice to potential entrepreneurs while also being a cracking read (it was all bank freebie list-fodder prior to Beermat). The cornerstones and the need for a mentor are now entrepreneurial mainstays and the advice on funding (hold on to your equity) worth the cover price alone.


  • Never Bet the Farm, Anthony Iaquinto and Stephen Spinelli. Too many books focus on the entrepreneurial giants: Branson, Jobs, Gates, Sam Walton etc. But what about us mere mortals? Iaquinto and Spinelli set out 15 principles for start-up entrepreneurs, including the need for realism, the joy of bootstrapping and the fact successful entrepreneurs are risk managers not risk takers (hence the title).


  • Start It Up, Luke Johnson. Along with his previous work The Maverick, this is an entertaining mix of thoughts and ideas from one of the UK’s best known serial entrepreneurs (and Sunday Times columnist). The widest range of subjects are attacked with gusto, insight and optimism. Johnson pulls no punches – the point is to make a profit. But his message that entrepreneurialism is great fun is infectious.


  • The $100 Start Up, Chris Guillebeau. More bootstrapping advice from this highly-readable and curiously empathetic “quit the rat race” bestseller. The book begins “Dear Boss, I’m writing to let you know that your services are no longer required” and goes on to extort passion, happiness, simplicity and free thinking. Lots of examples of how ordinary people have achieved extraordinary things in startup land.


  • Life’s a Pitch, Roger Mavity, Stephen Bayley. Having a great idea is easy. Execution more difficult. Selling the idea to those that matter – customers, investors, partners – is hardest of all, especially given that many entrepreneurs are introverts by nature. Mavity and Bayley turn up the heat – make no mistake, this bit’s critical – while deconstructing the process using irreverence and wit.


  • From Vision to Exit, Guy Rigby. Time to get serious. What makes a good business great? And how should a great business grow and, in time, be sold? Having the right strategy is essential, as is developing and pursuing an executable plan. Guy Rigby, Smith & Williamson’s entrepreneurial guru, certainly knows his onions – and his carrot and bananas too.

Robert Kelsey is the author of What’s Stopping You? and The Outside Edge, and deputy chairman of the Centre for Entrepreneurs


Groups to avoid: the moaning canteen gang


I call them the “moaning canteen gang” – that coterie within any sizeable company that hates their employer. They’re certain their bosses can do no right – and are vocal in letting everyone know: advertising their disgruntlement – usually during breaks – like a badge of honour.

The moaning canteen gang is a tight unit. It knows who’s onside and who’s not with respect to its core function of feeling justified in its complaints. Yet, like all organisms, its goal is to multiply – this time through recruitment (usually of the young and impressionable). Yet – make no mistake – they’re a disaster for any burgeoning career. Despite the bosom-buddy welcome, the moaning canteen gang is a career cul-de-sac. As an entity, it’s one to neatly sidestep (though not to antagonise).

In fact, I received an early education regarding the mixed blessing of joining the moaning canteen gang. My first job, as a supermarket Saturday shelf-stacker, had a fissure running right through it: between the full-timers and the part-timers. The full-timers were older, less educated and with a negative outlook compounded by years of doing something they disliked for people they didn’t trust. Meanwhile, us part-timers – often sixth-formers or students – were younger, more confident and saw this as no more than beer money for Saturday nights (usually spent trying to snog each other). Indeed, we enjoyed the job: it was more fun than classes and books (involving lift and cage races, cardboard cutting skills and lots of warehouse and shop-floor banter).

Yet the full-timers detested us. They occupied the best tables in the canteen and barked angrily if we transgressed their unstated rules (such as claiming the newer drafts game or complete chess set, or returning to work a minute too early). It was an antagonism that bemused me – at least until I was offered full-time work for the summer. Overnight I was pressured into becoming part of the moaning canteen gang. I was enticed by insights into the senior management’s proclivities (some highly personal), but also cajoled into pacing the work (now full-time in the warehouse) and into strictly observing any job demarcations.

And, soon enough, I too became irritated on a Thursday evening when the part-timers arrived to cover evening opening. They were just too cheerful, too noisy, too enthusiastic – and certainly too fast. They disrupted the pervading sense of indifference in the canteen and corrupted the lackadaisical pace of work – established to bridge the time between breaks with only the minimum expenditure in effort.

Eventually, the head warehouseman found me staring at the outside world through an air-conditioning grill and declared I’d probably had enough of the windowless warehouse: it was time to move on. Anyway, the moaning canteen gang had decided I wasn’t one of them after all (I liked the senior staff too much) – leaving me (yet again) the outsider.

Of course, this was 30 years ago. The supermarket is now a Burger King, with the canteen gang almost certainly all retired. Yet my guess is their moaning got them nowhere – just reinforcing their overall discontent with their lot. Meanwhile, the evening-and-Saturday kids – only a minority of which were Uni bound – will have taken their enthusiasm with them wherever they went, and now have their own moaning canteen gangs to contend with.








10 tips for difficult meetings


It’s that time of year again. When clients call us in for make-or-break meetings. Pens hover over future budget lines: shall we, shan’t we – less or more, growth or decline? One false move and an account can be lost. Three or four false moves and it could be curtains for our small but beautiful business.

The pressure alone can lead to mistakes. But, as is my way with such things, I’ve tried to rationalise what I used to see as a terrifying and life-threatening process. I’ve developed a 10 point plan for dealing with difficult meetings, which – in my case – are the current round of do-or-die client sessions likely to fill my diary between now and January 1st.

1) Stay focused on the objective. In this case, the goal is to retain or even grow the account. Given this, any other consideration has more to do with pride, vanity or even (perhaps especially) personal insecurities. Staying goal-focused depersonalises the meeting, removes the emotion, and concentrates the mind.

2) Stay positive. I once arrived on a date convinced I was about to be chucked by my girlfriend, which made me horribly defensive and, in fact, awful company. Guess what? I proved myself right. Would the result have been different if I’d behaved better? If I’d been positive and open – pretending this was the best date both she and I were ever likely to have? Who knows: but the result could have been no worse. So be upbeat (both on a date and in a meeting). Act as if you’re assuming the best – and enjoying the encounter: it may just sway a 50:50 (or even 40:60) decision your way.

3) Smile – radiate happiness. How you feel inside is irrelevant. It’s all about the image you project, which should be one of happiness no matter what happens. Even if fired, try and smile (not easy, I realise). Sure, you can feign surprise (fire us? You sure you’ve got that right?). But don’t melt into misery, or you’ll just convince them they’ve made the right choice (the same applies when dating, by the way). And as you arrive – with everything to play for – smiling your enthusiasm is an absolute must. What a joy it is to be in your lobby etc.

4) Avoid becoming defensive. This seems obvious, given the above. But it’s very easy to slip into defensiveness – not least because they’ll have a different perspective of any mistakes that may have blighted the year. It’s human nature to defend ourselves when attacked. Yet it’s also human nature to retrospectively twist facts in our favour. So absorbing the blame, no matter where it truly belongs, may just have the opposite effect – making them confess their contribution to any issues. Under it all, they’ll know when you’re taking the bullet, and they’ll be silently grateful.

5) Seek mutual agreement where possible. No matter how tough the meeting – no matter what the failings and accusations and diverging views – there will be common ground. Finding that ground is vitally important. In fact, it should be your first and foremost meeting tactic: get on the same page as them. In this respect, the management technique of the “shit sandwich” works well: i.e. focusing on the good stuff before dealing with any issues – and then quickly getting back to the good stuff.

6) Look for the win:win (and use that expression). I love the expression win:win because it’s indisputable. How could anyone not want a win:win outcome? So state that as your goal, and use the expression liberally. Yet focus on their win first. What constitutes victory for them, and how can that be achieved? That’s the route to your win. Indeed, if you state that their win is your win, you’ll be half way home.

7) Don’t seek to solve issues that don’t need to be solved. One of my biggest failings, I’m afraid. I go in mentally armed to deal with all the issues I think may crop up – and when they don’t I bring them up anyway! If it’s not an issue for them, it’s not an issue for you: and count it as a silent victory for your excellent prep anyway.

8) Forget about pride – except theirs of course. Empires have been destroyed through pride – wars have been lost and economies broken. Pride is one of the worst failings in humans and is a disaster in business. So leave your pride for the end result (take pride in that) and – in the meeting – make sure that the only pride that matters is theirs.

9) Act like someone people can work with. When it comes to service providers such as us, the decision very often comes down to chemistry. They’re looking across the table wondering whether this is someone they can work with. So act like that person. This doesn’t mean you should abandon professional pride (or professionalism, given that we’re avoiding pride). But it does mean you shouldn’t hide behind process or professional gobbledegook to make yourself seem important. Ultimately, they want a partner – not someone that pompously takes refuge behind their professional qualifications the moment problems arise.

10) Listen intently. Any bull-in-a-china-shop sales approach (of the sort seen on The Apprentice) will almost certainly backfire in these sorts of meetings. Enthusiasm is important but it’s a keenness to hear, and then align with, their story that matters. As with nearly all the points above, this is one I have to constantly pull myself up on, wanting to get my keenness across. Yet the more they talk the more they’ll feel the meeting went well. In fact, say nothing and just listen – and they’ll likely forgive you all your failings.

One last point on difficult meetings. In all my years of sitting in airless rooms around a table of executives, I can remember only a handful of truly difficult situations (and most of those were as a banker). If a client wants you out, they’ll usually tell you on the phone – or at least make it agenda item number one for the meeting. If something else is raised first – no matter how bad you think things have gotten – you can assume the account lives on to fight another day: so don’t blow it by responding badly.



Come and hear me speak at the Southwold Way With Words Festival on November 8th 2015.