From 0 to 57: lessons learned from management

I was 25 when I managed my first direct report. I’d always thought line management was something I’d wanted to do and probably like most that age, thought managing people was the only way I’d progress professionally.

It didn’t last long.

My direct report was great - young, kind, enthusiastic, and unbelievably driven. However, as a first-time manager, I was awkward giving feedback, would get frustrated when things weren’t exactly the way I would have done them, and being responsible for another employee just wasn’t something that sat naturally with me.

Around 3-4 months into my line management gig, I decided it wasn’t for me, and thought “s**t - how do I progress now?”

So, I handed in my notice and went traveling for 9 months (while freelancing).

I’m starting with this story for two reasons:

1. It led me to The Alliance (back in 2019 I was freelance copywriting for Product Marketing Alliance), and
2. I still find my reaction from 2018 funny given where I’m at now - responsible for 57 employees, which equates to half of The Alliance’s total workforce!

To this day, I’ve never read a management book, taken any training, or any kind of professional development when it comes to people management… although now I’m writing this, I’m thinking I probably should. 😅

That said, I’m proud of what I’ve achieved, and I’d like to think my teams feel the support, respect, and empowerment any great manager should provide.

So, today, I wanted to jot down some unapologetically honest musings from the last 3-4 years:

• Characteristics I did and didn’t carryforwards from previous managers - and why.
• Lessons I’ve learned on the job (often the hard way).
• Traits I respect and try my best to apply every single day.
• Personal hurdles I’ve had to overcome to be successful in my role.

Before I dive in, for a quick bit of context, here’s a zoomed-out view of the current teams I manage/oversee:

Leadership lessons from previous managers.

Never be above getting stuck in.

In a previous role, we were going through a huge data enrichment backdating job. We needed to speak to every single client (20,000+) and verify the details we had on file, as well as collect new data.

I’ll never forget how impressed I (and others in the marketing department) was when the CMO rolled his sleeves up and got stuck in on his commute (train) and in his evenings.

We’d hired in a bunch of temp interns to help with the task but I really admired him for chipping in and doing what needed to be done to get the job done.

This always stuck with me and is something I definitely adopt. When we’re under-resourced, I’m writing, building, and sending emails myself. Last year when we moved ESPs, I was moving all the data and rebuilding all the workflows.

It’s important to show you don’t think you’re above the duties you inevitably once carried out - because you’re not. You’re only as good as your team and you shouldn’t expect your team to do something you’re unwilling to do yourself.

Know your stuff.

I once had a previous manager who was incredibly kind and caring. I always felt valued and I knew they’d be there if I needed them.

However, they didn’t have expertise in my domain - copywriting. As a result, I didn’t feel pushed, I lacked in-depth feedback, and I had no one to turn to when brainstorming ideas or tackling skill-specific challenges.

This put a strain on our relationship and stunted my growth.

The lesson I carried forward here, is that I knew I wanted to be the type of manager that knew their s**t, stayed on top of trends/best practices/moves in the market, provides meaningful feedback, and helps their teams push ideas and strategies forwards.

Be firm (while maintaining fairness).

I once had a manager who was known for being nice. Everyone would say it. But in some ways, they were too nice.

They didn’t hold their own and assert their ideas/thoughts in a confident/authoritative way, and as a result, in the nicest possible way, they’d get walked over.

So, while I try to carry their niceness forward, I also carry forward doing a 180 on their approach to communication and collaboration. I endeavor to be assertive about what I want/need/like/don’t like, etc. - all the while being nice, of course.

Don’t bulls!$t.

Final trip down memory lane. The manager that bulls!$tted their way through every meeting.

Don’t get me wrong, I get the whole office politics thing (there was a lot of it in some of my previous orgs), but when you’re lying about what you’ve done, what you haven’t done, who’s done what, and so on, in front of your direct reports, it can quickly lead to distrust.

If they’re saying this when I am here, what are they saying when I’m not?

Trust is everything and can be instantly broken, and as a manager, it’s your role to ensure your words and your behavior build trust - not break it.

I appreciate none of the above are groundbreaking, but I think one of the biggest things I’ve learned about management is that it’s not mind-blowingly complex stuff.

It’s about consistently following basic best practices, and in the day-to-day (especially when the pressure’s on), keeping these kinda things front and center can often slip, so it’s always good to re-hear them!

The importance of building a creative culture as a CMO

In this article, I’m going over the best insights from my interviews with CMOs and marketing leaders on creative cultures, along with some findings from my own research.

CMO AllianceWill Whitham

Leadership lessons I’ve learned on the job.

So for the next portion of this blog, I want to focus on a non-exhaustive list of stuff I learned on the job. If you’re a manager you’ll know you learn something new almost every day, but these are just a few I’ve cherrypicked because once I came to terms with them, they had some of the biggest impacts.

Feedback is a positive thing.

I mentioned right at the start that with my very first direct report, I didn’t really enjoy the feedback part of the role - and this remained for probably my first 12-18 months of being with The Alliance, if I’m being totally honest. Of course, I still gave it, but I wasn’t comfortable doing it.

Positive feedback was always uber rewarding to give for obvious reasons, but when it came to the constructive, I probably held back for fear of making people ‘feel bad’.

This damaged them and me.

A combination of repetition and also rethinking and reframing how feedback is given really helped me overcome this and I now see feedback as a really positive and powerful part of my role.

It helps the people I’m working with improve.

It helps me look at things from a different perspective when my feedback’s challenged.

And it helps me get the end result I’m after.

For me, when I’m giving feedback, I’ll always:

• Find at least one piece of the work to compliment
• Always thank someone for the time they’ve invested on the job already
• Re-iterate the end objective of the brief at hand
• Clearly and kindly explain why X, Y, and Z don’t quite align with that objective
• Give pointers/share examples of how to implement this feedback moving forwards.

Again, super simple stuff. But good to remind yourself of when you’re squeezing in feedback between the other 649 things on your plate.

Letting go is hard.

The better you are at what you do, the less you get to do it.

This can be the hardest thing about management. You’re good at what you do, which is why you progress. But then the more you progress, the further away you become from actually doing what you love (in my case, copywriting).

This took me a long time to get to grips with and is actually why I’m writing this blog - to make sure I can find an outlet for what I love and keep my skills sharp.

Not everyone necessarily misses doing the doing, and if you don’t, good on you! But if you do, my advice would be to find a way to squeeze some of it in on the side, that way you get the best of both worlds.

You can’t be involved in everything.

Tied to the above point, it took me way too long to take a step back from the day-to-day.

Rewind around 3.5 years when I was managing around 6/7 copywriters while building out Product Marketing Alliance’s first membership plans and courses. At the time, I was still trying to proof every single blog post before it got published.

Why? Partly because I’m probably a bit of a perfectionist. I hated the thought of anything going out that wasn’t just right.

It wasn’t till I was in my first annual review and I got pulled up on it because (quite rightly) it wasn’t sustainable, scalable, or allowing me to focus my time on the more strategic pieces elsewhere.

Josie (The Alliance’s COO) reframed it for me: removing yourself from every proofing process puts more accountability on others and if they know you’re not going to be there to spot X, Y, or Z edit, they’ll be that much more attentive to spotting it themselves.

So I implemented a proofing buddy system and moved to spot-checking the odd blog after it’d been published instead.

And guess what happened when I removed myself from the proofing processes? Nothing. Everything still ran absolutely fine.

The best ideas come in groups.

Around 12-18 months into my stint at The Alliance, I got the nickname ‘the oracle’. Because I’d been with the company since day one and had been involved in so much of the business, I obviously had an awful lot of internal knowledge and became a bit of a go-to - which is where the name spawned from.

Subconsciously, for a while, this led me to feel like I had to know everything or I wouldn’t be viewed the same.

As the company grew, I felt I had to still know everything, and I thought I needed to be solely responsible for ideas.

Both, on reflection, were just plain silly.

Switching out of that mindset and understanding that just because you’re in a senior role with lots of responsibility doesn’t mean you have to come up with everything yourself to prove yourself, was a big one.

The best ideas come in groups and empowering your team to generate those ideas instead is just as much of a testament to your skills as a manager as coming up with shiny new ideas by yourself all the time.

Recruitment and retention are some of the most valuable hours you’ll spend.

I’m just gonna put it out there: no one gets into management for the love of recruitment. 🤷

It’s time-consuming and often, quite frankly, can just feel like dead time till you find that right match.

Now I’ve been involved in an awful lot of recruitment over the last four years (hopefully 0-57 employees says it all!), but it was only in the last 18 months or so that I saw it for what it was - the most valuable part of what you do.

You can’t achieve your goals without incredible people, and you can’t recruit or retain incredible people without investing time with no expectation of anything in return.

TL;DR: making recruitment a priority vs ‘that thing you do quickly before you log off’ was a really important mindset shift for me.

Be clear on your expectations.

Now this is a recent one. We’re currently doing a bunch of work with a company called People Collective, and in a recent call, we were talking about expectations, mainly in the context that more often than not, expectations are unwritten and unsaid.

Which when you think about it, is mad, right?

Your expectations of your employees and their expectations of you are the foundation of strong and positive working relationships, so not verbalizing, and not formalizing them just doesn’t make sense.

On the back of this, I recently did an exercise with my direct reports:

1. They let me know what they think my expectations of them are,
2. I let them know what I think their expectations of me are, and
3. We meet and discuss anything either party think is missed or unclear.

This clarity has been great for alignment and is something I’ll be looking to do with all new hires moving forwards, too.

Management characteristics that are important to me.

Every manager has their own style. No two leaders are the same and an important part of being a leader, is understanding what’s important to you and holding yourself accountable to living and breathing them every single day.

So, in this section of this very long blog, I’ll be chatting through the characteristics that I feel are important to my leadership style.

Be real - and don’t take yourself too seriously.

I’m a CMO. It goes without saying I have a very serious role, carry a heavy burden of responsibility, and feel that stress - some days more than others.

However, that doesn’t mean I’m a robot, I can’t have a laugh, and I need to act ‘professional’ 9-5.

When we have a Christmas party, I’ll let my hair down and get a wee bit too drunk.

Literally a few weeks ago, I fell out of bed in the middle of the night 😂. So the next morning, instead of saying ‘good morning’ to the marketing team, I told them.

Obviously, there are boundaries, but I love showing my teams the real me, and I hope that in being a bit silly and setting an example that I don’t take myself too seriously, they’ll feel they can let their guard down, too - we spend so many hours of our lives at our desks, we may as well try and have a laugh together while we’re there.

Praise good work.

Good work doesn’t need to mean bringing in $XXXX in deals (although that’s obvs great too).

It can be an idea, a way of wording an email, someone going out of their way to help others, staying late to deliver on X project…the list goes on.

If you’re in a position of responsibility, a big part of that responsibility is giving praise and creating an environment whereby people feel valued and that they too can speak up to endorse others - the more people who do this, the better.

Around ~9 months ago, I started a super simple ‘Friday shoutout’ on Slack. Every Friday, I’d publicly give a big thank you/well done to someone different and it got fantastic feedback.

Since then, the volume of shoutouts across the company, across every department, has significantly increased. Every week, in some form of Slack channel, there are at least a couple of people highlighting the incredible work people in the organization are doing and it’s been a real value-add to the organization’s culture.

I’m proud that I helped kickstart and contribute to this. If you haven’t already, I really recommend being intentional about how and how often you’re publicly praising work and starting an initiative of your own.

Honesty = trust + growth.

As I’ve grown into myself and my role, I’ve become comfortable being nothing but honest.

If someone’s fluffed up, I take the responsibility seriously of ensuring that (in a positive way) they know about it, and more importantly, they know how to avoid it moving forwards.

I believe in honesty of giving credit where credit’s due (in previous companies, I’ve witnessed many a manager taking credit for their team’s ideas - I really disagree with this).

Honest feedback. Honest opinions. Honest communication.

Honesty = trust.

Trust = the bedrock of any relationship.

Empowerment.

Don’t get worried if/when your team starts thinking about ideas/solutions/questions before you do - it’s a testament to your skills as a manager.

I’m not gonna lie, I used to struggle with this and worried it meant my value was decreasing in tandem with theirs increasing. I now realize how blinkin’ stupid this was.

Empower your reports to make decisions. Empower them to question your choices (no one’s always right!). Empower them to do things differently. Empower them to have a voice, say, and opinion - period.

This is easy to do - but even easier to break.

All it takes is one call or one message shooting someone down for everyone in the group to second guess whether or not they should say that thing or ask that question next time, and when people start thinking like this, everyone misses out - so even if you don’t agree with something, be super intentional with how you respond/turn it down.

Add value along the way.

This one probably sounds like an obvious one, but I’ve had previous managers that didn’t have enough expertise in my domain to be able to add genuine value to my work or ideas.

To me, despite how many departments I’m spread across, it’s really important to have both breadth and depth of knowledge so that I can provide actionable feedback, build upon existing ideas, iron out process kinks, etc.

I don’t ever want to be the type of manager that loses touch so I make it my mission to ensure that fine balance between freeing up my time to focus on strategy, but also staying abreast of the smaller details and day-to-day.

I’ve managed to do this up till this point (15x communities, 57x people in my teams, overseeing 4x departments, 110+ company headcount) - who knows what I’ll be saying if this all doubles again!

Show a genuine interest.

Take that 5/10 minutes at the start of your weekly catchup to check in on people. If you know someone went to the movies the night before, ask them how it was. If they’ve got a holiday coming up, ask what they’ve got planned. If their mom was ill last week, ask them how she’s doing. If someone’s a little quieter than normal, ask if everything’s okay.

To me, it’s really important to show a genuine interest in all the things that happen outside of the 9-5 - not just because it’s what you should do, but because I genuinely am! We’re all so different - different hobbies, different personalities, different perspectives, and understanding this helps you understand people better.

Plus, I’m pretty sure caring about your team - and showing them you care, never harmed anyone. 🙂

Stand up for your and your team’s decisions.

Is there anything worse than having a great idea, sharing it with your manager, getting on a call with a few others, and it getting disregarded without a fight?

Or making a change to a process/campaign, perhaps it not working out, and then getting thrown under the bus by your boss?

I’m sure I don’t always succeed as best I’d like, but I try my damned best to ensure I’m always in my team’s corner - I think it’s important to support the failed experiments (aka learning), support their ideas and advocate for their implementation, and fend for them not just in your 1:1, but in front of others.

If people know they have your support, they’ll likely feel much more comfortable next time they want to pitch an idea, next time something doesn’t quite go to plan, etc.

Positive energy breeds positive energy.

Now this one I know I don’t always succeed at (it’s a work in progress)...

Let’s not sugarcoat it - being a CMO is stressful. Huge revenue responsibility, endless meetings, constant context switching, non-stop juggling, people management, strategy, sign-off, etc, etc.,

However, I try my best never to let this show. When I was thinking about this the other day I kind of likened it to my days of being a waitress. Some days, I’d turn up to work and I just wasn’t in the mood (probs argued with my college boyfriend earlier in the day), regardless, I’d slap a smile on my face and serve them pints like nothing had happened - even when I didn’t feel like it.

Rightly or wrongly, I take this approach to my role as a CMO. If I’m feeling particularly stressed, or I’ve just had a heated Slack debate with Rich (CEO) (#jokingnotjoking) I try my best not to let it show in my next call, or pass that emotion onto anyone else.

To me, it’s important that pressure isn’t passed onto my reports for a couple of reasons:

1. They don’t worry they can’t add to that pressure with any of their own challenges/questions, and
2. They don’t fear that progression in the org means they’ll feel that pressure.

My aspiration is to always be approachable, always be composed, and always energize those around me.

The elements of a great marketing leader

We’ve created a periodic table of elements detailing everything that a great marketing leader needs to have a handle on.

CMO AllianceWill Whitham

Personal challenges I’ve experienced along the way.

I certainly wouldn’t say my route CMO was typical. I hadn’t had any previous marketing leadership roles, it was unexpected, and it was quick.

I went from freelance copywriting to CMO in the space of three years and while I wouldn’t change a thing, it did result in some pretty steep experiential shifts - here are a few of the key ones.

Coming to terms with not writing anymore.

My bread and butter had been copywriting. I love to write and the more senior I got within The Alliance, as you’d expect, the less and less I got to do what I love - and this was hard to come to terms with at first, and really alien to me.

Due to some resource constraints, to date, I have actually still been dabbling in some copy and am still writing and building the odd email for some of our communities (which although can feel like a pain because I don’t have the time, I must confess, I secretly enjoy).

However, those resource constraints will soon be gone which means I’ll be pretty much fully removed. Here are a couple of things I’m doing to satiate my love of writing:

• More blogs like this outside of work! This is enabling me to keep my copywriting skills sharp and write freely at the weekend/in the evenings, as and when the mood takes me.
• I mentioned earlier in this post that it’s important to me to keep close to the day-to-day and add value, and I thrive off being involved in projects and contributing to the messaging we’re using, and this also helps me to keep that spark alive.

Imposter syndrome is REAL.

As I said at the start of this section - my entry to my CMO role was quick and unexpected. I imagine every first-time CMO feels imposter syndrome, but I kinda feel like mine was enhanced.

It took months and months and months for me to talk myself out of it. I’d put myself down and think to myself, surely I’m not good enough for this. Surely this is too soon. Surely I need more on-the-job experience to be able to do this.

While I’m over this hurdle now, I can’t say those doubts never come in. I’ve hired people with many more years of work experience under their belt, and sometimes I’ll think to myself ‘how am I going to add value to this person?’, but do you know what, I always do. And each time I do, my confidence continues to grow.

The one thing this has taught me is that you don’t need alllllll the years on the job to be good at what you do. I became CMO at 29 with less than eight years of professional experience behind me - but that doesn’t matter.

I feel like I’m getting a bit soppy at this point, but don’t let your age, or your experience, or ‘the norm’ dictate what you’re ready for. Take the opportunities where they come, seize them, apply yourself, and you’ll be surprised at what you achieve.

Confidence is key.

I chuckle at myself when I think about what my confidence is like now, versus what it was like when I was younger.

Six years ago, if I were in a work meeting I’d be too shy to speak up and represent myself.

10 years ago, if I went to the hair salon, I’d barely even speak while I was sat in the chair.

Today, I chair tons of meetings, I’m uber vocal in the ones I attend, and I’m not afraid to put my ideas, challenges, thoughts, and feedback forwards.

I’ve not intentionally done anything to grow my confidence and even when I first started at The Alliance it was a million miles away from what it is now, but it’s just been a byproduct of continuously putting myself in those situations and rising to the role.

Now I’m not saying my confidence is perfect or where I’d like it to be by any stretch - I still have a long way to go. Public speaking is NOT my jam, is something I’ve actively avoided my entire life, but is something I recognize I need to tackle head-on as part of my role - which is why I’m forcing myself into uncomfortable (to me) situations moving forwards - like getting involved in our CMO Summits.

Don’t be a yes man.

No one ever got to be in a leadership role by saying yes to everything, and/or agreeing with everything.

Within my first 12 months at The Alliance, I probably did this. But as my confidence, knowledge, and skills increased, so did my ability to push back - not in a combative way, but it’s important to challenge decisions to make sure we’re actually making the right ones.

And I’m now comfortable doing this regardless of who it’s with or what it’s about. I obviously report to the CEO (Rich) and I’m sure he’s stopped reading by this point, but I’m just as comfortable challenging him (much to his annoyance) as I am a direct report - and I think this is super important.

What I want to get better at.

Okay, last section of a crazy long read (thanks for sticking with me if you’re still here!).

I said I was going to be candid so I wanted to finish on 2x areas I still don’t think I’m all that good at, but am actively working on.

Coping with pressure.

I can let pressure get to me both physically and emotionally. If something’s not going to plan, numbers aren’t where they need to be, I’ve got too much on, or I’m getting frustrated by X, Y, or Z, etc., my reflex reaction is effing and jeffing to my partner over tea or letting it eat away at me in and outside of work - which takes its toll.

Here’s what I’ve been doing lately (with success) to try and combat this:

• Last year, as part of our employee benefits package, we rolled out access to Oliva. I’ve taken full advantage of this and speak to someone every other week about all sorts of topics that are important to me, one of which is coping mechanisms for stress. This has been a fantastic support and resource and something I plan on continuing with for life.
• Journaling. I try to do this every night before I go to bed and writing out and rationalizing my worries helps me put them into perspective and approach them with a different mindset next time a pressure trigger arises.
• Work-life balance. Up until a few months ago, I’d work crazy hours - which I certainly don’t advocate for in my team. As a result, I’d be pretty mentally and physically drained throughout the week, which obviously impacts your emotional response in stressful situations. Being strict with my boundaries has not impacted my output whatsoever, but it’s made me happier, healthier, and more laser-focused when I am online.

Knowledge-sharing.

Your greatest skill, power, and achievement as a manager is enabling those you manage to think like you, connect the dots you connect, make decisions on your behalf, solve problems on your behalf, and build relationships and strategies on your behalf.

Whilst I don’t think I’m terrible at this, I do think I could be better in some areas.

My issue with some of these areas in which I want to pass knowledge down is that I kinda do things on autopilot. I don’t always have a clear thought-out process or a clever formula, I just do it or know it because I’ve been so entrenched in every aspect of the organization for the last four years.

This is something I want to actively overcome over the next few months so that I can continue to devolve responsibility to the amazing senior managers and leaders I have reporting to me.

Phwoar, that was a long one…

If you’re reading this, you made it. 🙌

Which I’m guessing means you’ve gathered some kind of value from this short essay. I didn’t realize how much I had to say on this topic till I started writing and I’d love to hear your thoughts.

What did you resonate with? What were your biggest struggles/learnings? What do you think I’m missing? If you wanna continue the conversation, I’d love to connect on LinkedIn.

Does your journey into marketing leadership align with Bryony's? Are there lessons you've learned that other aspiring leaders need to know about? Share your stories, and get the advice you need in a global network of CMOs and marketing leaders: The CMO Alliance Community Slack channel.