Richard Con­way shares what he be­lieves are the four big­gest headaches for busi­ness own­ers, and the best way to deal with them.


We all know that start­ing a busi­ness – and keep­ing a busi­ness run­ning – is tough. If it wasn’t, ev­ery­one would do it. In­stead, we’re left with the pas­sion­ate, dili­gent ones who are pre­pared to weather the storms and keep on fight­ing for­ward. From chal­lenges con­cern­ing cash­flow, to the per­sonal and sen­si­tive is­sues sur­round­ing peo­ple, busi­ness can be fraught with risk (and a few headaches!) on the way to re­ward.

Be­ing an en­tre­pre­neur and a busi­ness owner doubt­less means mak­ing hard de­ci­sions, and those who suc­ceed most def­i­nitely master (or at least im­prove on) learn­ing from their mis­takes.

This month, I take a look at what I con­sider to be the four big­gest chal­lenges fac­ing en­trepreneurs, and how I have over­come these. 1. CON­CERN­ING CASH­FLOW Money doesn’t make you happy, but it cer­tainly makes the world go round – and never is this truer than in the world of busi­ness. Big or small, I’m yet to come across a busi­ness that doesn’t con­cern it­self with cash­flow. It’s a jug­gling act. Re­gard­less of whether you get paid, you have to pay staff and ex­penses – in­clud­ing things like your of­fice lease – up­front.

You may know your busi­ness’s rev­enue, and its fore­casted turnover or profit, but your true cash­flow day-to-day within your busi­ness re­ally comes down to tim­ing.

In most busi­nesses, at least in pro­fes­sional ser­vices, you do the work and the cus­tomer re­ceives the de­liv­er­able, and then you in­voice them for it. Con­sider turn­ing this model on its head and billing in ad­vance of the work tak­ing place or, if it’s a large project, struc­ture progress pay­ments through­out the life­cy­cle of the project, so you’re min­imis­ing how much re­source you are out­lay­ing be­fore you see any money.

If your rev­enue is re­cur­ring, en­cour­age your cus­tomers or clients to set up direct deb­its or au­to­matic pay­ments. Not only is this eas­ier for them, it en­sures you get paid on time ev­ery time, with­out hav­ing to rely on a per­son do­ing the trans­ac­tion when they should. 2. PROB­LEMS WITH PEO­PLE Your com­pany cul­ture, and the sub­se­quent per­son­al­i­ties and at­ti­tudes of your peo­ple, per­me­ate ev­ery as­pect of your busi­ness.

You’ll know this when you’ve had an in­ter­ac­tion with a busi­ness or brand and found the per­son dif­fi­cult or dis­en­gaged; it de­grades your whole ex­pe­ri­ence. Now imag­ine what those ‘poi­sonous’ peo­ple are do­ing in­ter­nally. I think of those ‘bad ap­ples’ like rip­ples in a pool; they may start as one cen­tral spot, but their ef­fect spreads out in ever-wi­den­ing cir­cles of dis­tur­bance.

One of the key learn­ings I have un­cov­ered in busi­ness is the vi­tal im­por­tance of deal­ing with peo­ple prob­lems quickly, which is not al­ways easy for peo­ple who don’t like con­fronta­tion.

I’m one of those peo­ple so, for me, it is im­por­tant to take as many pre­ven­ta­tive mea­sures as I can – and this comes down to get­ting the cul­ture right. We do this in a num­ber of ways – through team build­ing ac­tiv­i­ties and shared lunches; with our an­nual strat­egy day, dur­ing which ev­ery­one is in­volved and heard, and where we iden­tify real, ac­tion­able out­puts and fol­low through on them; through anony­mous polls of staff that fo­cus on con­tin­ual im­prove­ments the busi­ness can make; by in­cen­tivis­ing the types of be­hav­iours we want to see more of; and, im­por­tantly, by em­pow­er­ing and trust­ing our peo­ple to de­liver.

Good peo­ple, who are in the right kind of en­vi­ron­ment, will have ideas and cre­ate pos­i­tive stuff within your busi­ness with­out you even know­ing – so cre­ate a cul­ture that en­cour­ages this. 3. MAK­ING (AND LEARN­ING FROM) MIS­TAKES I know we’re stray­ing into cliché ter­ri­tory here, but bear with me. It’s to­tally nor­mal to make mis­takes, and that in it­self is not the prob­lem. A prob­lem arises when we don’t learn from them. To be suc­cess­ful in busi­ness, you need to be able to pivot (who else is pic­tur­ing that iconic Friends episode here?). Se­ri­ously though, the abil­ity to change tack is crit­i­cal, and these piv­ots of­ten come from ini­tially mak­ing mis­takes.

Em­brace mis­takes and find a way to deal with them; it all comes down to how quickly you re­act. If it’s some­one in your team that makes a mis­take, the first thing I fo­cus on is not throw­ing blame. It’s a nat­u­ral and in­stinc­tual re­ac­tion to do so, but one that needs to be over­come.

Take a breath and trans­par­ently work to­wards a so­lu­tion. Those who feel blamed are likely to be­come on edge and make more mis­takes from feel­ing un­der pres­sure, which isn’t good for any­body.

Take ac­tion in a so­lu­tion-fo­cused way to start with, and then cir­cle back to the les­son with the peo­ple in­volved.

It’s not al­ways easy to find the les­son when things have gone wrong, and you may strug­gle to see what you could have done dif­fer­ently. Here I find that re­mov­ing your­self helps. You need time away from the of­fice and space to think; I find that’s what brings per­spec­tive and even in my re­lax­ation time, my mind tends to be work­ing.

I try to book at least a cou­ple of in­ter­na­tional con­fer­ences a year; be­yond be­ing tax de­ductible hol­i­days, they pro­vide an op­por­tu­nity to think about my busi­ness. It’s there that I have the most pro­found in­sights.

Throw things around at man­age­ment and board meet­ings too; other smart peo­ple around you are vi­tal, and this is what I think is the real value of pro­fes­sional or­gan­i­sa­tions, like the En­trepreneurs Or­gan­i­sa­tion (EO). 4. TACK­LING TOUGH DE­CI­SIONS If you’ve started a busi­ness, chances are the buck stops with you and that’s bound to mean that you, and some­times you alone, have to deal with some tricky de­ci­sions.

This is some­thing that I used to put off, but I’ve learnt from ex­pe­ri­ence that of­ten the ram­i­fi­ca­tions of leav­ing some­thing are big­ger than if I had dealt with it more quickly.

You do get bet­ter at this as­pect of busi­ness over time; it’s part of de­vel­op­ing true lead­er­ship skills.

Be open and re­cep­tive to those around you, as of­ten they can tell if some­thing isn’t work­ing, or clue you into where you might have to make a hard call. A good, trusted team around you en­ables you to have ex­tra eyes on things. It also helps to com­mit you to a course of ac­tion, once you have de­cided; vo­cal­is­ing your choice and the re­sult­ing path to oth­ers pro­vides the im­pe­tus to fol­low through.

Over­all though, trust your gut – it very rarely leads you wrong.

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