The Operators series is for people in operating roles in high-growth startup and scaleups. Written from experience. For founders and their leadership teams, plus those talented motivated people who are interested in the bigger picture.

The first post of Operators was Managing Chaos.

It was first intentionally because when you’re scaling a business managing chaos is just a fact of life. It is perhaps the defining experience and feeling of scaling. So you gotta manage it. That or basically die :shrug:

Fortunately, chaos has a friendlier twin: Momentum.

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Momentum

Remember when you were 17. OK, 16. (Ok, what 14? Wow… ) And you were walking towards the door of the nightclub. The club you really had to get into. You can hear the music. You can see a partial view into the club’s interior. You can smell adventure (lol). Eye contact with the bouncers. That burst of extra adrenaline. YA-ya-ya-YAAAA. Now pause right there: it was at this exact point I used to imagine I was walking through the door. No slowing. No subtle inertia. No pre-conceived rejection, unwittingly conveyed by subconscious cues of body language. A mental trick to our own adolescent brains – ‘I’m sailing through yes I am and that bouncer is gonna have to ask me to stop and and and I’m innnnnn’.

Momentum and a fake sense of confidence (or a fake ID) carried us through.

Just earlier in cold British sunshine this morning my younger boy – new to the game of rugby this year – catches the ball, runs at the opposition and just before contact, slows. In rugby you need to run through people. Or over them. Or if you’re clever, around them.  (Imagine American Football, less the body armor and the constant stops in play.) He’s caught, contained. That fraction of a second of hesitation was everything. A quick cue from a coach and in the next play he runs at and through the opposition. Legs pumping. No imagined slowing down. No trace of hesitance to allow the opposition to tackle. Momentum.

Sales people understand momentum. They sense for the heat and velocity of a deal, of a customer in-store, intuiting for that ‘propensity to buy’. Of course, great sales people don’t just feel it – they create it. One to one, asking questions that deliver a cascade of yeses. Or in the more sophisticated and subtle world of selling to groups of buyers in the enterprise, they build a groundswell amongst the prospects’ stakeholders. Through their orchestrated sales campaign they build positivity, an unfair bias and alignment across the boundaries of client-side functions and politics. And how to pace to it – when to go with the customer’s flow, when to speed it up. Momentum.

Momentum is magic in business. I really believe that.

It is waves of progress upon waves of progress. It’s ‘oh, and another (good) thing’. It’s rolling goddamn thunder. It is launch followed by client win followed by awards followed by big new hire followed by another client win. It’s you saying to the inside world of staff, investors, one another – that latter one of self-belief in the leadership is perhaps most important in some ways – and of course to the outside world: ‘hold on to your motherfucking hats, WE’RE WINNING, WE’RE MAKING THIS HAPPEN, AND EVEN MORE IS COMING’.

I reckon momentum is a big piece of the game in building a successful growth company. And as a CMO or a CEO especially, it’s one of the biggest opportunities you have. Even better, it’s free of charge. I certainly see it as one of the biggest things I can do to support a company.

How to create momentum

1. Look for it
2. Make the links explicit
3. Timing is everything
4. If you don’t hype, who will?

Let’s get to it.

1. Look for it

Momentum has to be real. To convince you and your team, let alone analysts or potential clients or investors. I mean, you can put some sizzle on it but people sense bullshit and hate vaporware and if you don’t know it and feel it nobody will.

So to create a sense of company momentum, you need to first spot the waves. Externally they might be things like:

• New product announcements
• BIG customer wins
• Acquisitions
• Funding announcements
• New talent / leadership / board members
• Partnerships
• Big events
• Awards and endorsements (but good ones, you guyz)
• Major publicity
• Real impressive results – sales growth, outcomes, revenues, data you’re willing to share and stand by and if necessary prove

Internally, you’ll know what big moments of success are. It will vary massively according to your circumstances.

So spot them. See them. Name them. Commit to them. And proceed to step 2.

2. Make the links explicit

This is important. Probably the most important and directly controllable lever you have in creating Momentum.

See not the one wave in isolation. Look back and figure out when your last ‘big announcement’ was. Look ahead and figure out when the next will be. If you can, the one after that too. Put the waves together into a sequence of positives in your head and then make these explicit to the people you’re communicating with.

What you’re aiming to do is help the company bounce a one-off success and ping pong it into another in the near-future to create the sense of a string of successes. Then you pull something else forward or new out of the bag, and now you have a 1-2-3 and yes! the flywheel of positive momentum is spinning.

Yours is the company on peoples’ lips, front of mind, the one with extra heat.

Develop the habit to always talk about momentum in series rather than one-off. Mention the multiple examples of mojo. One or two positive items is just unrelated good news. Three or four is undeniable momentum. So in your internal all-hands or in the press release, reference the previous big announcement – ‘coming off the back of our recent successful fundraise…’ / ‘following last week’s amazing news about BIG BRAND CLIENT signing up for 2 years…’. Help others see what you see. Let no positive milestone stand alone!

And if it helps and you’re happy to, preview what’s next ‘and with our [committed next big thing] just around the corner, even more good news is coming’. It feels good. And it’s real. And it’s momentum.

About that flywheel: it takes more effort to get started than it does to keep it whirring. Don’t let it slow. (Note to self: Will, remember this always, even though you know it, never forget it).

3. Timing is everything

Be smart about timing. If two good waves are about to crash at the same time, make sure that makes sense in your head – ‘could we pull them apart by just a few weeks?’.

Consider your most important trading periods – figure out how momentum can carry you into this with a surge of an unfair advantage over the competition. Get out the blocks before the rest of the pack. Do the unexpected!

Thoughtfully stage the waves. Whilst plenty of this is opportunistic, some of these you can gently steer or even orchestrated. Great strategy is about coherence. Wouldn’t it be cool if this good news could happen at the same time as the major industry event or landed just a week after we told the team about the good news on new hires.

And pay attention to the mood. Of your staff. Of your customers. Of the market. Let that be an input to this too. Not in some kind of bankrupt ‘we gotta get good news to them, desperately!’ way. Just as another input to your timing.

There’s no playbook for this stuff. It’s just putting a little bit of thought into it and trusting yourself because frankly anyone can do it. All I’m suggesting is that developing the habit of thinking about when you want the fair winds to blow will help you maximize the boost that they give you.

4. If you don’t hype, who will?

This one pisses me off.

There’s this idea that you should quietly earnestly build rather than hype the effort and care from your team, their hard fought victories, the sweet occasional relief of some things going well and great product being shipped. In this line of thinking, the logic goes that the world – perhaps internally, your leadership, your board, or externally an influential client group, or journalists and analysts covering your space – will take care of noticing your hard work and if you’re lucky, send the appropriate rewards, credit, publicity. In some circles, and you will sometimes strangely feel it amongst your own, there is this dismissive view of people promoting their hard work. Seriously, fuck that.

Don’t let others foibles and insecurities or your own internal critic get in the way of the whole team’s greater good.

Most of the time you’re more down on what you’re doing than your fans and happy customers are because you see what didn’t get shipped, what isn’t where you want it to be, yet. In the team environment, the people around you are occupied with their role, their work, chopping the wood and need a helpful reminder to step back and see their collective progress. They also will want that permission, that space and that validation from you as a leader or from someone that isn’t their doubtful second-guessing self.

Plus, if we’re honest here amongst friends, most of the time the broader market or public essentially don’t care. In the nicest possible way, they don’t have enough attention available to pay to you. If you’re not putting yourselves on the line and saying ‘THIS MATTERS. I ask of you your attention. I won’t waste it’ well, most people won’t bother.

So call out the positives, the big chunks of progress, and don’t hide them. Because if you don’t hype it, who will?

1. Look for it
2. Make the links explicit
3. Timing is everything
4. If you don’t hype, who will?

Momentum puts a multiplier on your growth. It creates inbound you can’t attribute – resumés, leads, invitations for coffees with investors, unexpected outreach from partners. It creates a glue in your team that you can’t buy – a feeling that they’re in a good place and on a winning team. It increases sales outcomes and accelerates them too, and decreases sales and marketing expenses. It quite fundamentally lifts the value of the business in boardrooms and on the street and the feeling of momentum makes working more fun.

And the best thing is it’s free.

I love momentum. 

Post #2 in The Operators Series. Feedback welcome ~ WM

After 5 and half years as one of the leadership team scaling up Brandwatch I’ve learned lots more about growth, chaos, ambiguity, resilience, culture, business, people, hiring/firing, org design, marketing, sales, boards and investors and so on.

In that time, we’ve grown from 130 people to 550, 5x’d revenue, made 3 successful acquisitions, are completing 1 merger, have expanded globally and hit EBITDA profitability now with $100m in recurring revenues. I’ve been lucky, I’ve been involved in all of that.

And when it comes to scaling tech businesses like this, you can find a lot of very good stuff written by investors/VCs. (Maybe they’ve got more time than the rest of us :)). But there’s not much out there from operators, and when I mentioned to one of our previous board members that I was impressed with how smart a new investor seemed to be, this board member countered immediately with a wry smile: ‘Yes! He is very smart, Will! But he is not an operator… We are the operators. We make it happen. Don’t forget this’.

I haven’t forgotten that respect for the operator. So this series is for the Operators.

By operators, I mean people in operating roles in high-growth startup and scaleups. Usually the CXO and VPs. The founders and their leadership teams, plus – importantly, to me – the many smart motivated people that you get in every decent high performing company who are relentlessly learning themselves and care about the bigger picture, even if they haven’t reached formal ‘leadership’ roles just yet.

These people are doing the work of growing companies on the inside.

I take a broader view than just a classical CMO perspective, mainly because in my tenure I’ve played a wider role than my title of CMO, secondly because I think that’s more interesting selfishly, and thirdly because it’s more applicable to more of you than a deeper by-CMO-for-CMOs viewpoint.

—

Managing Chaos

Everything is already exaggerated in a small company trying to grow at 50-100-150%+ a year.

You’re already trying to do something differently to how everyone currently does it. Growth creates constant challenges.

An experienced SaaS CFO we interviewed once used the metaphor of one of those shaped balloons for kids you get from street entertainers, at parties and theme parks – twisted into shape to resemble a poodle or a light sabre. This CFO pointed out that growing a SaaS company, you tend to find that any one time a particular part of the business will be squeezing and swelling out of sync with the others. Whether it’s new customers to be onboarded, new inbound leads from a territory that aren’t being followed up, sudden demands on systems capacity as new users stream into a successful launch, a ton of open requisitions that the recruiters and managers suddenly need to fill. And whilst you focus on solving that problem and squeeze improvements back into a manageable and potentially new shape, new problems swell and start to burst out elsewhere. POP!

It’s all interconnected.

Plus you’re a small ship sailing big seas, where the global environment is already characterized by VUCA – gotta love that Volatility, Uncertainty, Complexity, Ambiguity, eh. A context that is further amplified when you have limited resources, no precedence or process, entrepreneurial leadership, and when everything by its nature is ‘the first time its been done’.

So fundamental to leading a growth company is managing chaos.

Managing chaos is not about avoiding it or eliminating it. You just can’t. In my experience, the chaos moves too fast. It is a rogue shapeshifting force and pops up in new places, manifested in new shapes. The causes of it are not just internal and therefore even controllable – they come from the outside, sometimes in waves or combinations that feel overwhelming, on top of the many crises you inevitably also create yourselves.

In crisis management circles the saying of hopeful British politicians and public relations practitioners is ‘today’s front page news is tomorrow’s fish and chip paper’. In growth companies too, yesterday’s crisis is a distant memory – and you’re often already on to the next one. (Sidenote: agency people know what this is like. Which is why I think agencies are a great hiring ground for startup/scaleup talent that’s got grit and resilience and know how to smile when the going gets, well, dramatic.).

So what can you do, apart from just get through it?

1. Communicate
2. Drive out ambiguity
3. Harness what is useful
4. Watch energy levels
5. Find the wins

Let’s take them one at time.

1. Communicate through chaos

The biggest mistakes I’ve been involved have absolutely been made worse by poor communication. Usually internally. And usually just not thinking to communicate, and with the best intentions, just ploughing forwards with the ‘bias for action’ that everyone loves to cultivate/hire for/role model around. But whilst this is mainly about internal communication, it is true for external comms in moments of crisis too.

With managing chaos, I’ve learned that the worse it is, the more I need to quickly and efficiently keep a cross-section of people informed about. I pick a group that I think represent the broad edges of the issue at hand. I look for functional and geographical representation. And I keep it fast, lean and – when things happen over a day or two – provide updates.

The reflex you want to create in yourself and others is simple: if the shit’s going down, start communicating as you also assess and start to fix the problems.

2. Drive out ambiguity

In times of chaos and challenge, ambiguity is not my friend.

Yes, we have to live with ambiguity in growth businesses – but where possible, when the pressure is on, we need to drive it out. The last two most stressful big announcements I worked on kept tipping over from one day to the next. It wasn’t possible for us to know when THE BIG THING was happening, but we knew it was 99% happening. That uncertainty was really hard. It kept us in a state of limbo – unable to trigger actions with other groups of people, shuffling calendars and priorities on a day to day basis, ripples of disruption that cascaded across teams and continents, our small group containing the pressure of what comes next, without the relief of ‘anddddddd GO!’. Nothing you can do in that situation.

But when I’m working in chaos, I’m consciously trying to find the ambiguities that CAN be controlled, that can be named, that can be defined and boxed in and closed off.

I chase them down, these grey areas. I hate them. I push for short, functional documents that are shared by the working group to force the definition and agreement of subjects. (Documenting things doesn’t seem particularly fashionable these days but I don’t give a shit. If we write it down, we understand it better and can agree/disagree more specifically). I get people together if they seem to be saying different things. I push as hard as I can for clarity and simplicity. The goal is to force out the unknowns. Define, eliminate, name what’s left. And if you do this too, it will massively help. It will reduce stress for the whole team, and as the knowns increase, the remaining unknowns feel and are much more manageable. The problem you’re trying to solve lifts out of the fog, while everything else falls away.

3. Harness what is useful

Like in judo, yes? The assailant comes at you. Big, ugly looking, hairy like me. You crouch, pull their sleeve closer towards you, tilt your hips, start to twist and oops, the big ugly assailant is in the air, rolling across your shoulders and – BLAMM – lying flat on their back. Cool, bro.

Crises and chaos have an energy about them. Harness it.

I’ve found chaotic times to be hugely positive learning experiences for me and people working with me. We’ve had developing team members take career-defining steps forward in their growth through painful projects and exhausting, high pressured phases in the company’s history. Time and pressure creates diamonds – cheesy yes. Also true.

So I try and if possible take moments when they arise to make sure the people working with me are seeing that. It helps them to see it as a growth experience as well as scary cool big assed thing to work on. It helps them to see more explicitly their learning as it happens. And it helps us recap, regroup and really bake in those learnings afterwards. ‘So what did you learn?’.

Secondly, these moments can also create strong internal impetus for change. Don’t waste that. Provoke the conversation that needed to happen. Propose the way to avoid this in future. Challenge the bullshit status quo.

And these moments of chaos and tribulation can also motivate your team in a David v Goliath way. Screw the competition. Fight the incumbent pressures and mindsets. Ship the product better, faster, shinier. Find a unique design solution to the seemingly ‘all is lost and we have no resources, no time and no hope’.

Harness what is useful.

4. Watch energy levels

As an operator and a leader, if you’re managing too much chaos too much of the time, you’re gonna feel its toll.

This is not a good or sustainable way to operate. The nice list above is the choice highlights amongst what is generally really hard work and not brilliantly good for you. The bad stuff – well that’s everything else. The stress of this is unhealthy. Me personally? I’m coming off the back of a serious rolling phase of managing different chaoses (is there actually a plural for chaos?) and it’s not been good for me. I need to reset. I can feel it in my energy levels, see it in my moods, other people are reporting it back to me, asking me if I’m OK (normally they don’t!). And I know my team and the people around me have been depleted too.

I gotta get my lifejacket on, and then after or if possible at the same time make sure they get theirs on too. Some mindfulness. Take some breaks. Connect with people outside. Sharing the problem. Exercising. Reading before bed. Simple healthy habits are what work for me.

So we need to notice that. We/I need to increase the check ins – ‘how you doing?’ is simple but good. ‘Please make sure you take the time back’ is not just fair and reasonable, it’s fucking important. Rest. Reset. Don’t let your people or your self burn out. I’ve learned through outdoor pursuits and through working under pressured that actually silence can be the worst sign. Look out for people quietly drowning, or those that have gone unusually quiet. It’s often not a good sign, and only costs a quick check-in to see if it’s quietly productive or silently sinking.

This modern business phrase you may have started hearing of ‘being athletes’ (lol), well at least let’s take something good from it: rest is a crucial and fundamental part of an athlete’s training program. And thankfully, we are living in a time where mental health is finally coming out of the shadows and margins and being bravely put center stage. Makes it easier to get on the table.

I believe one of life’s worthwhile pursuits and an essential part of a successful operator’s tool kit is locating and returning to the recuperating strategies that work for ones self. And encouraging and coaching those around them to find theirs too.

5. Find the wins

Finally and most obviously, sustain yourself and those around you by finding the wins. (My current team may laugh darkly at this one – they probably don’t think I do this enough/at all, but I do). Celebrate survival. The passing of a crisis. The growth in experience and new skills and capacities. A very wise lady I’ve occasionally worked with at Hyper Island recently said ‘life will never move this slowly again’, and she’s right, so we will might as well enjoy the chaos or at least the pauses in between!

There you have it. Some thoughts on Managing Chaos. And the first post in a weekly series for Operators. Feedback welcome.

~ WM

PS. On hitting publish on this, I’m reminded that part of my inspiration to do this was fellow Brandwatcher James Stanier’s wonderful The Engineering Manager. Thanks for the inspo to get writing again, James.