Sales methodologies month has begun, and we’re starting with the Challenger Sale.

This one is all about helping customers think differently — which sounds noble until you realize it also means saying, “Are we sure that’s actually the problem?” without getting escorted out of the room.

In this episode, we talk about:

• How Challenger is built around teaching, tailoring, and taking control
• Why it works best in complex sales
• The danger of using a heavyweight methodology on a lightweight opportunity
• How consultative selling can uncover the real business issue hiding behind the obvious one
  

We also get into the Digital Momentum Summit and how to think about ROI across prospects, clients, partners, and brand amplification — because apparently “it felt useful” is not always accepted by finance.

A useful one for anyone selling complex work, running events, or trying to prove that business development is more than just a mysterious cloud of coffees, conversations, and hopeful follow-ups.

#Sales #BusinessDevelopment #ChallengerSale #ConsultativeSelling #B2BMarketing #TeaAndTimbits

Complex selling sounds like it should require a giant tech stack, seven dashboards, and at least one acronym nobody fully understands.

But in this episode, we discovered something slightly annoying: the best tools are often the simplest ones.

We talked about:

– borrowing ideas from completely different industries
– using design thinking to untangle messy business problems
– reading broadly, not just another sales book
– showing up at events and learning from real conversations
– using note-takers, AI transcription, or even the ancient technology known as “pen and paper”
– managing complex sales more like projects
– turning repeated customer friction points into useful content

The slightly humbling conclusion?

Complex sales do not always need complex tools. They need curiosity, structure, perspective, and a willingness to say, “I don’t know — who can help?”

Which is far less glamorous than a new platform subscription, but probably cheaper. And harder to lose than an Apple Pencil.

Complex selling is never just about “the buyer” and “the seller.”

We wish it were. It would make life much easier, and we could probably all spend less time in meetings pretending the spreadsheet is “basically under control.”

In this episode, we talk about stakeholder engagement — the people inside and outside the deal who can quietly make everything work… or loudly make everything fall apart.

That includes executives, delivery teams, partners, suppliers, finance, operations, customer service, and sometimes the person who appears halfway through the process with a very strong opinion and absolutely no context.

The big takeaway?

Stakeholder management does not have to be perfect. But it does have to exist.

Even a simple list of who is involved, what they care about, what they are worried about, and how they affect the outcome can prevent a lot of firefighting later.

And if you are always firefighting, well… we may have accidentally diagnosed the problem.

In this week’s episode, we get into:

• Why stakeholder management goes beyond executive selling
• How to uncover hidden risks before they become expensive surprises
• Why internal delivery teams need to be involved earlier
• How partners and suppliers shape the customer experience
• Why “known unknowns” are far better than “unknown unknowns”

Have a listen, especially if your complex sales process currently relies on optimism, crossed fingers, and a heroic amount of Slack messages.

This week, we’re recording together in London for a rare in-person episode, which naturally means things go slightly off the rails before we even get to the topic.

We kick things off with a story about hiring event security, where we learned the hard way that ticking qualification boxes doesn’t always mean someone can actually do the job. Turns out “having the badge” and “being able to climb stairs without needing a lie down” are apparently separate competencies.

From there, we dive into the world of complex selling and executive selling — and why most big deals are won (or lost) long before the final proposal lands.

We explore:

• Why executive selling is more than just presenting to senior leadership
• How to use your own executives as part of the sales strategy
• The importance of coaching leadership teams before customer meetings
• Why one uninformed stakeholder can derail an entire deal
• How to tactfully expand conversations to include hidden decision-makers
• The role of context, repetition, and preparation in complex sales
• Why executives need exposure to real customer conversations

Along the way, we also accidentally turn the conversation into relationship advice and realise that executive communication skills might be just as useful at home as they are in the boardroom.

It’s a practical, slightly chaotic conversation about influence, credibility, preparation, and the human side of complex deals.

This week, we dive headfirst into the world of complex deals and team selling — and discover that the secret to winning big opportunities isn’t bringing eleven people and a 300-slide deck into a meeting. In fact… it’s usually the opposite.

We explore why complex deals are more often lost to internal chaos than to competitors, how healthy businesses create healthier sales processes, and why clarity beats noise every single time. Along the way, we talk about overloaded pipelines, managing urgency without panic, executive sponsorship, customer alignment, and the importance of having one person truly “own” the opportunity.

There’s also a cautionary tale involving eleven people heading into a defense contractor meeting… which thankfully became two people and three slides before anyone got hurt.

As always, we manage to make complex sales sound both strategic and mildly ridiculous — which, honestly, is probably the most accurate description of enterprise selling anyone’s ever come up with.

In this bonus episode, we doubled down on what actually drives healthy teams and results—and spoiler alert: it’s not luck, and it’s definitely not another fancy spreadsheet.

We kicked things off with a simple but powerful reminder: just showing up (literally, in person) can unlock opportunities you didn’t even know existed. Turns out, a casual “while you’re here…” can be worth six figures. Not bad for a day out of the office.

From there, we unpacked our slightly cheesy but surprisingly effective framework: capability, culture, capacity, and consistency. We talked about why consistency is usually the first thing to slip (guilty), and how without it, everything else quietly falls apart.

We also got into the habit most teams get wrong—only reviewing what went badly. Instead, we made the case for digging into wins and understanding what actually worked (because let’s be honest, “we lost on price” tells you absolutely nothing).

And finally, we brought it all together with one key idea: healthy businesses are built by design, not by accident. No shortcuts, no magic—just deliberate effort, reflection, and a bit of resilience when things don’t go to plan.

If you’ve been chasing better results without stepping back to look at how you’re operating, this one’s for you.

This week, we wrap up our “Healthy Team, Healthy Results” series with a tools episode—but not the kind you’d expect.

We kick things off with a story that perfectly proves why getting out from behind the screen still matters. What started as a routine 15-minute client meeting turned into a game-changing discovery… all because we were physically in the room. Turns out, you can’t replicate hallway chats and off-script insights on Zoom (we’ve tried—awkwardly).

From there, we dig into tools—not just the usual suspects like CRMs and calendars—but the ones that actually support culture, collaboration, and long-term business health. Think corporate social media used properly (yes, really), peer-to-peer recognition platforms, learning systems that don’t make you want to cry, and even… office chairs.

The big takeaway? Tools don’t fix broken processes—they amplify whatever discipline you already have. So if things are messy… well… congratulations, you’ve just bought yourself a faster mess.

We used to think “healthy body” in business conversations meant… well… eating a salad and pretending we enjoy it.

Turns out, it’s a bit more important than that.

In our latest episode, we got into something that doesn’t get talked about enough:
> Leaders set the tone — not just with strategy, but with how they live and work

If you’re constantly stressed, skipping breaks, and powering through holidays… guess what your team thinks “normal” looks like?

A few things we discussed:

• Why blocking vacation time in advance actually works
• The difference between customer service and customer experience (and why it matters more than you think)
• How a lack of structure quietly leads to burnout, bad decisions, and takeout-for-the-third-time-this-week energy
• And why “treating yourself” can become a slippery slope if you’re not careful

None of this is revolutionary.
But it is the stuff that quietly separates healthy teams from chaotic ones.

We’re not perfect at it (far from it), but we’re trying to be more intentional — and this episode was a good reminder.

If you’ve ever said “I’ll take a break after this week”… this one’s for you.

#Leadership #TeamCulture #Wellbeing #BusinessGrowth #CustomerExperience