Surviving Sales Leadership

You cannot motivate an unmotivated sales rep, because motivation is self-generated. 

What a leader can do is work out what "unmotivated" is actually hiding. 

A rep who is not making enough calls might lack the skill, might have the skill but not the confidence, or might not have the process support to do the job properly. Those are three different problems that look identical from the outside, and most leaders act on the label instead of the cause.

Steve Myers is a sales leadership coach at MySalesCoach with 19 years of coaching behind him. Tim Ogle is a MySalesCoach coach with 30 years in sales, split between selling and turning businesses around.

In this episode, host Tom Boston sits with them to discuss why trying to motivate people usually fails, how to tell a motivation problem from a skill problem, and what to do long before a PIP enters the conversation.

📥 Download the Modern Revenue Leader's Sales Coaching Manual
 https://bit.ly/3QTbqsJ

You'll learn:

• Why performance is what happens and motivation is why it happens, and why that distinction changes how you manage
• How to tell whether a rep's drop in activity is a motivation issue, a skill issue or a process issue
• Why the carrot and the stick have both stopped working, and what replaced them
• The difference between quota and target, and why every rep needs their own number for their own reasons
• How to run a structured goal setting conversation that gets past "I want a big house and a nice car"
• How to break a ten year personal goal down into what a rep needs to do in the next eight hours
• Why you change behaviour first and let belief catch up, rather than waiting to feel ready

Steve Myers

Steve spent 20 years in global IT sales before moving into coaching, and started his career selling Encyclopaedia Britannica door to door. He works with sales leaders on structured goal setting, accountability, and the process for getting reps to act outside their current belief system.

Connect with Steve Myers on LinkedIn 🔗

Tim Ogle

Tim has split his career roughly evenly between selling directly and leading, transforming and changing businesses. He works with leaders on setting expectations, holding people accountable without tipping into micromanagement, and using assessment data to have the conversations most leaders avoid.

Connect with Tim Ogle on LinkedIn 🔗

Surviving Sales Leadership sessions help sales leaders tackle their biggest sales challenges in short, focused bursts. We aim to get most episodes done in 30 minutes or less. New episodes every two weeks. Brought to you by MySalesCoach.

Follow MySalesCoach on LinkedIn

Most sales leaders hire on gut feel. Gut feel only predicts top performers 20% of the time — and the cost of a mis-hire goes far beyond a wasted salary. It drains coaching energy, damages team morale, and locks leaders into developing the wrong person instead of their best people.

📥 Download the Modern Revenue Leader's Sales Coaching Manual
 https://bit.ly/3QTbqsJ

In this episode, Bryan Mulry sits with them to discuss why sales hiring keeps going wrong — and what a structured, low-risk hiring process looks like from talent pool to first 90 days.

You'll learn:

• Why gut feel is a reliable signal in one direction only — and how to use it correctly
• How to build a talent pool before you need it, using LinkedIn content, referrals, and events
• What a competency-based scorecard looks like and why it's the only way to avoid decision paralysis
• Why the offer process starts at the first conversation, not when you send the contract
• How to onboard a new hire so the first 90 days set them up to perform — not scramble
• Why the transition from onboarding manager to coach is the moment most leaders drop the ball
• The real cost of a bad sales hire — beyond the salary

Elaine Tyler is the CEO and founder of Venetrix, placing sales talent into fast-growth SaaS, cybersecurity, and fintech businesses in London and the US. With 20+ years of experience, she helps hiring managers build processes that cut mis-hire risk from the first conversation.
Connect with Elaine on LinkedIn 🔗

Tim Ogle is a sales coach and transformation specialist at MySalesCoach. He works with companies to hire the right people, develop the ones they already have, and build the coaching habits that turn new starters into consistent performers.
Connect with Tim on LinkedIn 🔗

Surviving Sales Leadership sessions help sales leaders tackle their biggest sales challenges in short, focused bursts - we aim to get most episodes done in 30 minutes or less. New episodes every two weeks. Subscribe so you don't miss one. Brought to you by MySalesCoach.

Follow MySalesCoach on LinkedIn

Surviving Sales Leadership is brought to you by MySalesCoach.

Most sales leaders know AI is changing how teams sell. The ones falling behind aren't short on ambition - they're short on a starting point. Research shows sales reps spend 75-80% of their time on admin rather than selling, and AI is the fastest route to flipping that ratio. The three highest-impact places to start are prospect research, personalised outreach, and call analysis.

📥 Download the Modern Revenue Leader's Sales Coaching Manual: https://bit.ly/3QTbqsJ

Tom Ridley is a Sales Coach at MySalesCoach with deep expertise in sales leadership transformation, AI-enabled performance, and GTM strategy. Richard Smith is Head of Growth at MySalesCoach and brings a practitioner's honest perspective on where most sales teams actually are with AI adoption.

In this episode, host Ollie Whitfield sits with them to discuss the three AI use cases sales leaders should prioritise right now - and exactly how to start.

You'll learn:

• Why 71% of employers now prioritise AI skills over experience - and what that means for your team
• How sales reps are spending 75-80% of their time on admin, and how AI closes that gap
• How to use Perplexity for prospect research that used to take 15-20 minutes per account
• How to build a personalised outreach engine using tools like Reggie.ai, Tuesday, or ChatGPT projects
• Why call transcripts are the most underused data asset in most sales teams
• How to use call transcripts to build meeting prep slides in under a minute
• How to pull prospect language from call transcripts and turn it into your best prospecting messaging

Tom Ridley is a Sales Coach at MySalesCoach specialising in sales leadership transformation, AI-enabled performance, and GTM strategy. He works with B2B sales leaders across SaaS and technology businesses to build high-performing teams and coaching cultures that scale. Connect with Tom Ridley on LinkedIn 🔗

Rich Smith is Head of Growth at MySalesCoach and an experienced B2B sales leader who posts daily on LinkedIn about sales, leadership, and what's actually working in modern selling. Connect with Rich Smith on LinkedIn 🔗

Surviving Sales Leadership sessions help sales leaders tackle their biggest sales challenges in short, focused bursts - we aim to get most episodes done in 30 minutes or less. 

New episodes every two weeks. Subscribe so you don't miss one. 

Watch this on Youtube here: https://youtu.be/SCXTO5V0H3E

Brought to you by MySalesCoach.

Follow MySalesCoach on LinkedIn

Most sales leaders treat LinkedIn as a brand exercise. Post a few times a week, get some likes from colleagues, move on. But the reps who are actually self-sourcing pipeline are using it completely differently - they're building their own SQL machine, turning engagement signals into warm conversations before they even pick up the phone.

📥 Download the Modern Revenue Leader's Sales Coaching Manual https://bit.ly/3QTbqsJ

Will Aitken built his entire outbound motion around LinkedIn across three different companies. Niraj Kapur has done 220+ videos and converts inquiries directly from them. Between them and host Tom Boston, there are over 170,000 LinkedIn followers on this episode.

In this episode, Will and Niraj sit down with our host Tom Boston to get into what that actually looks like in practice - the content strategy, the video outreach, and the personal vs professional balance that most reps get wrong.

In this episode:

• Why LinkedIn personal brand is an MQL list you build yourself - and take with you when you leave
• How Will uses LinkedIn content to warm up prospects already in his pipeline between stages
• Niraj's video outreach approach that generates direct inquiries and how he converts them
• The 80/20 rule for personal vs professional content and what happens when you get it wrong
• Why the algorithm matters far less than most people think
• How to use LinkedIn strategically for named accounts, not just broadcasting to the masses
• The one question to ask before posting anything: would your CEO share this?

About Surviving Sales Leadership:
Surviving Sales Leadership sessions help sales leaders tackle their biggest sales challenges in short, focused bursts - we aim to get most episodes done in 30 minutes or less.

New episodes fortnight. Subscribe so you don't miss one.
 
🌐 Episode page: https://www.mysalescoach.com/surviving-sales-leadership-home/how-sales-leaders-build-sql-machine-linkedin

🔗 Connect with Tom Boston on LinkedIn
🔗 Connect with Will Aitken on LinkedIn
🔗 Connect with Niraj Kapur on LinkedIn
🔗 Follow MySalesCoach on LinkedIn

About Will Aitken Will Aitken is a sales content creator and coach based in Canada, originally from Milton Keynes. He built his personal brand while working as an account executive and used it to generate his own pipeline - taking that audience with him across three different companies. He's known for honest, direct content about what actually works in sales.

About Niraj Kapur Niraj Kapur spent 25 years in sales before founding Everybody Works in Sales, a coaching business working with teams across the UK, Europe and North America. He's done over 220 LinkedIn videos and converts them directly into coaching clients.

Most sales leaders have sat across from a rep who's fully convinced a deal is closing. 
Champion engaged. 
Proposal out. 
Close date locked.
And they're wrong.

Richard Smith sits down with Chris Lingenfelter (VP Sales & CS, Level Up) and Nigel Arthur (former MD and SVP Sales, enterprise SaaS - now coach at MySalesCoach) to show exactly what separates pipeline from forecast - and how fast the difference becomes obvious when you ask the right questions.

They cover why emotion is the single biggest killer of forecast accuracy, what entry/exit criteria your CRM stages are probably missing, and why a rep who "feels really good" about a deal is a red flag, not a green light.

The session ends with a live deal review. Richard plays the rep. Nigel and Chris ask five questions. 

The deal doesn't make the forecast.

Find out which questions did it.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

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About this episode:

Ever had that feeling where your pipeline looks busy… but nothing’s actually moving? 
Yeah. Turns out, you’re not alone.

Sales leaders think stalled deals are a pipeline problem.

Sales reps are experiencing something very different.

In this episode, Ollie Whitfield sits down with Steve Myers, and John Richardson to unpack insights from analysing 5117 real sales coaching calls and what they reveal about why deals lose momentum.

The conversation exposes a gap between what salespeople ask for in coaching and what’s actually holding performance back. 

While most conversations focus on pipeline, deal progression, and “tips and tricks,” the real blockers often sit deeper—in decision process clarity, mindset, and how sales teams think about control in the deal. 

The episode explores why decision process dominates coaching conversations, why “closing” is often misunderstood, and how over-reliance on tactics masks underlying behavioural and mindset challenges. 

It also highlights the disconnect between prospecting responsibility and pipeline ownership, and how this impacts quota attainment and sales velocity.

This episode is essential listening for: VPs of Sales, Heads of Sales, Sales Managers and Revenue Leaders who are trying to improve sales coaching effectiveness, increase deal velocity, and build a stronger coaching culture that goes beyond surface-level tactics.

Brought to you by MySalesCoach.

Learn more about how we support leaders in building elite sales teams with our Sales Coaching Operating System:

www.mysalescoach.com

Simple comp plans are easy to explain. Bad comp plans are easy to regret.

This episode gets into the real damage sales leaders create when compensation becomes unclear, unfair, too clever, or easy to game.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

In this sales leadership lesson, Mike Pritchett of BuzzTrail and David Wilkins unpack what actually happens when comp plans drift away from the behaviours the business needs.

• Reps disengage fast when they cannot clearly see how they make money
• Changing comp after overachievement destroys trust and pushes good people out
• Complex plans create confusion, politics, and arguments over who deserves what
• Poorly designed incentives drive sandbagging, bad meetings, gaming, and low-value activity
• Too much disparity across reps creates distraction, resentment, and “why are they getting more than me?” conversations
• Team-based targets can hide poor performance and pull everyone toward mediocrity
• Commission-only setups sound attractive in startups, but make it harder to judge fit and build real team energy
• Small non-cash rewards can sometimes motivate better than taxed cash incentives
• Public recognition, competition, and simple scoreboards still matter because sales is hard and momentum matters

The core message is straightforward: compensation is not just about paying people. It shapes behaviour, trust, culture, focus, and performance. When leaders get it wrong, they do not just create payroll problems. They create distraction, resentment, short-term thinking, and a sales team that starts working the plan instead of working the market.

This episode is for VPs of Sales, Heads of Sales, SDR leaders, and founders trying to build comp plans that stay simple, reward the right actions, reduce internal friction, and help good reps perform without creating avoidable chaos.

• (00:00) - Start

Timestamps

00:00 Why simple comp plans outperform clever ones

08:35 The hidden damage of changing comp mid-year

16:42 Incentivising the wrong behaviour and how reps game the system

27:18 SDR and AE comp, quotas, territory fairness, and startup trade-offs

39:46 Why communal targets and uneven comp create resentment

48:58 Non-financial rewards, surprise incentives, and recognition that actually lands

Brought to you by MySalesCoach.

Learn more about how we support leaders in building elite and consistent sales teams:

www.mysalescoach.com

Everything feels like it’s moving—and nothing feels stable.

You’re expected to build a high-performing team while the ground keeps shifting beneath you.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

In this episode, Tom Boston and Emily Parker break down what it actually looks like to build and lead a sales team inside the chaos of SaaS—where strategy changes, expectations evolve, and pressure never lets up. 

This episode is for:

Sales leaders who are building or scaling teams in fast-moving environments, dealing with inconsistent performance, struggling with hiring decisions, or trying to maintain control and morale while everything around them changes.

Inside this sales leadership lesson:

• Feeling like you’ve “figured it out”… only for messaging, ICP, or strategy to change overnight
• Trying to lead with confidence when you’re figuring things out in real time yourself
• Translating top-down strategy into something your team actually understands and buys into
• Hiring people who look great on paper but can’t adapt when the environment shifts
• Managing high performers who resist structure and think results excuse behaviour
• Dealing with promotion pressure from reps who think they’re ready—but aren’t
• Keeping morale high when growth is messy, processes are broken, and support is limited
• Carrying extra roles (ops, enablement, HR) while still being accountable for performance
• Balancing autonomy with accountability without losing control of the team
• Building a team that complements each other—not just a group of similar performers

At its core, this episode is about the reality that SaaS growth is rarely clean. Leaders are expected to deliver results while navigating constant change, incomplete systems, and evolving expectations. The ones who succeed aren’t the ones with perfect plans—they’re the ones who can create clarity, build trust, and develop teams that adapt faster than the environment shifts.

• (00:00) - – Why building a sales team in SaaS still feels chaotic

04:30 – The real challenge: constant change + managing people through it

08:00 – Building a balanced team (and why hiring “more of the same” fails)

10:30 – Leading with clarity when the business keeps shifting

16:00 – Staying calm and building confidence through uncertainty

21:30 – Trust, autonomy, and setting boundaries with your team

25:00 – Hiring realities: coachability, resilience, and what actually matters

33:30 – Managing promotions, expectations, and team progression pressure

38:00 – What messy growth really looks like—and how to keep morale high

Brought to you by MySalesCoach.

Learn more about how we support leaders in building elite and consistent sales teams:

www.mysalescoach.com

Many sales managers focus on pipeline, activity, and numbers.

Top sales leaders focus on developing people.

Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

In this episode, Tom Boston sits down with Nia Woodhouse and Ollie Sharpe to explore the leadership behaviours, coaching habits, and decision-making that separate average sales management from truly high-performing sales leadership.

The conversation looks at how elite sales leaders structure coaching, build hiring processes, and create environments where reps consistently improve. Nia and Ollie explain why the best leaders separate performance management from skill development, ensuring that coaching sessions focus on mindset, skills, and long-term capability — not just forecast discussions.  

They also break down how top leaders set goals that are actually achievable by reverse engineering revenue targets into specific activity and performance milestones. Instead of chasing a big number without direction, great sales leaders help their teams build a clear roadmap that shows exactly how success will be achieved.  

The episode also explores hiring philosophy, emotional intelligence in leadership, and why the best leaders create trust by standing in front of their team when things go wrong — and standing behind them when they succeed.  

This episode is essential listening for VPs of Sales, Heads of Sales, Sales Managers, and Revenue Leaders who want to move beyond activity management and build teams that consistently perform, grow, and stay motivated.

• (00:00) - - How a leader’s habits shape the whole team

Timestamps

00:00 - How a leader’s habits shape the whole team

00:34 - Intro: what top sales leaders do differently

00:44 - What new sales leaders wish they knew before stepping up

03:22 - How top leaders hire: structure, skills, and culture add

09:15 - Interview red flags experienced leaders spot early

12:02 - Why pipeline reviews are not coaching

14:21 - How top leaders scale coaching with frameworks, not just advice

21:03 - Motivation, commitment, and what really drives performance

27:58 - Setting expectations without micromanaging

37:00 - What top sales leaders do best

Brought to you by MySalesCoach.

Learn more about how we support sales leaders in building and empowering elite teams:

www.mysalescoach.com

If deals keep stalling and the story is always “they’ve gone quiet,” the real issue usually showed up much earlier — and it often isn’t being said clearly in coaching.

PS.
Want to be a great coach for your team and drive results in the time you DO have for coaching?
Download the Modern Revenue Leader's Sales Coaching Manual

This session with Steve Myers and Richard Smith gets into the actual reasons deals don’t close, and how deal coaching can surface the truth without turning into a forecast grilling.

We break down how to diagnose what’s missing in the deal, validate what’s real vs assumed, and coach reps beyond surface-level reasons into compelling, evidence-backed buying drivers.

This is for you if you're a sales leader dealing with:

• “Close” deals that never close and pipelines full of hope instead of proof
• Reps who can’t clearly articulate why a prospect will actually buy
• Stalled opportunities where next steps were never properly locked in
• A coaching culture where people tell you what sounds good, not what’s true

In this episode, you’ll hear the deal-killers hiding in plain sight:

• Reps mistaking “they want X” for a real problem worth solving
• “I think…” language replacing evidence — and nobody challenging it properly
• Surface-level pain (“save time,” “be more efficient”) with no detail behind it
• Discovery that never gets to the full three levels of pain: symptom → business impact → how people feel about it
• No clear understanding of where budget comes from, how the decision gets made, or where veto power sits
• Leaders accepting the rep’s narrative without validating what’s actually happened
• Weak upfront contracting — so next steps aren’t agreed, meetings aren’t booked, and deals drift into silence
• Repeated stalls that look like a skills issue… but are really discomfort, need for approval, or fear of being too direct
• Keeping a deal alive when the best outcome is clarity to qualify out and redirect effort elsewhere

Most deals don’t fail at the end — they fail because the team never got the truth early enough. 

Great deal coaching creates the environment where the rep can say what’s missing, get specific about the gaps, and leave with clear actions — or the confidence to walk away.

Timestamps:

• 0:00 – 5:13 | Creating the conditions for truth: Removing agendas and power dynamics so the real issues surface
• 5:14 – 7:31 | Diagnosing what’s really going on: Buying journey context, decision process clarity, and validating the rep’s story
• 7:32 – 13:02 | The real reasons deals don’t close: Evidence vs belief, solution-language, and coaching to three levels of pain
• 13:03 – 18:10 | Repeat deal failure: Technical vs mindset problems, and why reps don’t use the skills they “know”
• 18:11 – 21:52 | Prep that prevents stalls: Meeting plans, upfront contracting, objectives, and keeping calls on track
• 21:53 – 24:05 | Outcomes that matter: Immediate next actions, strategic skill-building, confidence — and when to qualify out

If you’re a sales leader tired of chasing “almost” deals and want your coaching conversations to surface the truth faster — listen to this episode and start changing how your team diagnoses, not just how they close.

PS.
Want world class deal coaching for your team? We've got you.
Find out more here
https://www.mysalescoach.com/deal-coaching

Surviving Sales Leadership is brought to you by MySalesCoach.  

Learn more about how we support leaders in building elite and consistent sales teams:  

www.mysalescoach.com