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by Donald C. Kelly
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- Yesterday31 min
Why So Many Talented Women Never Make It to Leadership | Erika Chestnut - 2003
Many women in sales struggle with feeling like they’re not fully qualified for leadership roles, even when they’re already doing the work. That self-doubt can make it harder to pursue promotions and career growth. To help break this down, I invited leadership coach and tech executive Erika Chestnut to share the challenges women face when advancing their careers and how sales leaders can better support them.Meet Erika ChestnutErika Chestnut is a transformational leader with more than 25 years of experience in the tech industry. She is passionate about helping individuals and teams rethink leadership, communication, and workplace culture to create stronger performance and long-term success. Through coaching, leadership development, and strategic guidance, Erika equips professionals with practical tools to build confidence, strengthen relationships, and lead more effectively.The Confidence Gap Holding Women BackErika shares how often women underestimate their readiness for leadership opportunities. She explains that many women feel like they need to accomplish every requirement before applying for a promotion, while others are comfortable taking the leap much earlier.Erika also shares an exercise she uses with clients where they compare their current responsibilities to the role above them. In most cases, women are already doing 50% to 75% of the next position without realizing it.Many women feel pressure to constantly prove themselves through performance while still struggling to advocate for their own advancement. Erika explains how this mindset can keep high performers stuck, even when they are already operating at the next level in their careers.Why Leaders Need to Better Understand Communication StylesCommunication styles also play a major role in career growth. Erika explains how many leaders unintentionally overlook talented women because they communicate differently from more outspoken employees.She also shares how some employees naturally focus on details while leaders are often focused on outcomes. When communication styles do not align, high performers can easily be misunderstood or overlooked.Treat Your Career Like A BusinessErika shares advice on how women can become more intentional about career growth by treating their career like a business. Set goals, build relationships with mentors and stakeholders, and develop a strategy for long-term advancement instead of waiting to be noticed.“Success doesn’t come by copying somebody else. Success comes when you know who you are.” — Erika ChestnutResourcesConnect with Erika Chestnut on LinkedIn or visit her website to learn more about leadership development, career strategy, and building confidence as you grow into your next role.Keep track of your sales activity and boost your results with the Prospect Pro sales tool.Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.Visit Blue Mango Studios for help in creating podcast production content. Sponsorship OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by LinkedIn.Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the <a href="https://tsesales.typeform
- 4 days ago29 min
How To Help Enterprise Sellers Speak The Language of their Clients | Kevin Cope - 2002
show notes
- 1 weeks ago28 min
The Biggest Reason Why Your Sales Pipeline Is Not Converting As It Should | Gearoid Cox - 2001
show notes
- 1 weeks ago37 min
What 2,000 Sales Conversations Taught Me | Donald C. Kelly - 2000
show notes
- 2 weeks ago30 min
The Biggest Reason Why Your Sales Pipeline Is Not Converting As It Should | Wesleyne Whittaker - 1999
Should your demo and discovery call happen in the same meeting? If you’re combining the two, it may be the reason your pipeline is not converting the way you want it to.Wesleyne Whittaker, sales professional and author of Sales Reset, joins me to challenge how most teams run demos and discovery and why it might be the reason deals are stalling. She also shares practical frameworks from her book Sales Reset to help you run more effective discovery calls.Meet Wesleyne WhittakerWesleyne Whittaker is a sales strategist, coach, and author of Sales Reset. She’s known for helping sales professionals rethink how they approach conversations so they can stop going through the motions and start actually closing deals.What makes her approach stand out is how she blends mindset with real sales execution. She does not just talk about what to do. She shows you how to do it in a way that feels natural and effective.She works with sales teams across different industries, helping them run stronger discovery calls, ask better questions, and create demos that actually connect with buyers.At the core of her work is a simple idea. Sales is human to human. And when you focus on understanding people first, everything else starts to fall into place.Why Discovery Should Come FirstWesleyne believes deals begin to close during the discovery call. If that conversation is weak, your pipeline will reflect it.Instead of jumping straight into a demo, she explains that discovery should focus on listening. You should be talking about 20 percent of the time while your prospect does the rest.That is how you uncover the real problems, not just surface level requests.What an Effective Discovery Looks LikeA strong discovery call starts before the meeting even begins. Research the company, understand their environment, and come prepared with one key opening question.From there, let the conversation guide your follow ups. The goal is to identify three to five real challenges your solution can solve.When both sides are learning from each other, the conversation becomes valuable.How to Deliver a Demo That ConvertsOnce you understand the problem, your demo becomes simple. Connect each challenge to a specific feature.Avoid showing everything. Focus only on what matters to that buyer.When your demo feels tailored instead of generic, it becomes easier for prospects to see the value.“Don’t do your discovery and demo in one meeting. It’s better to cut a 30-minute call into 20 minutes and say, ‘Let’s reconnect so I can tailor this for you,’ than try to cram everything in.” — Wesleyne WhittakerResourcesGrab a copy of Sales Reset to learn how to run stronger discovery calls and close more deals, and don’t forget to connect with Wesleyne Whittaker on LinkedIn.Keep track of your sales activity and boost your results with the Prospect Pro sales tool.Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.Visit Blue Mango Studios for help in creating podcast production content. Sponsorship OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by LinkedIn.Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at <a href="https://business.linkedin.com/sales-solutions/cx/20/09/sales-navigator-podcast?src=re-pod&trk=tse&veh=tse&mcid=6
- 2 weeks ago16 min
Missed Quota Series: Prospecting With A Next Rather Than A Spear! | Donald C. Kelly - 1998
40% of a seller’s time is spent on prospecting. That’s a big investment, especially when a lot of it does not lead anywhere. So how do you make sure that time actually turns into real opportunities? Let’s break down how to prospect in a way that leads to conversations and closed deals.Leverage Intent and Relevant DataA big part of prospecting comes down to timing. You want to reach out when buyers are already looking for a solution.That is where intent data comes in. Tools like ZoomInfo and 6sense can help you identify prospects who are actively researching solutions like endpoint protection.When you do reach out, make it relevant. Speak directly to their industry and back it up with a recent success story from a similar company. That is what helps build credibility early.Utilize Advanced LinkedIn SearchingInstead of reaching out to everyone, focus on a smaller group of people who are more likely to respond.You can build a list of 30 to 40 individuals by narrowing your search. Look for people who are new in their roles or who have been active on LinkedIn in the past 30 days.You can also look at who they are connected to, especially if they follow industry influencers or are part of specific associations. That gives you a stronger starting point for outreach.Systematize ReferralsReferrals are one of the most overlooked opportunities in sales.Most prospects are open to giving referrals, but very few salespeople actually ask for them. That is a missed opportunity.Start making it part of your process. When you are working with a client, ask if they know others who are dealing with similar challenges. A simple ask can open the door to warmer conversations.Target Niche Local EventsNot every opportunity comes from online outreach. Smaller, more focused events can be a great way to connect with people directly.Think industry meetups or informal gatherings where conversations happen more naturally.These settings make it easier to build relationships and lead to introductions that feel more genuine.The Fortune Is in the Follow-UpEven when you get in front of the right people, it does not mean much if you do not follow up.A large percentage of event attendees have the authority to make buying decisions, yet most leads never receive any follow-up at all.That is where the real opportunity is. Following up within 12 to 24 hours and staying consistent with your outreach can be the difference between being remembered and being forgotten.“Nine out of ten prospects are willing to give a referral, but only about 11% of salespeople actually ask.” - Donald C. KellyResourcesDo you need help on getting more referrals? Check out episode 1976.Keep track of your sales activity and boost your results with the Prospect Pro sales tool.Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.Visit Blue Mango Studios for help in creating podcast production content.Sponsorship OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by LinkedIn.Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/l
- 3 weeks ago17 min
Missed Quota Series: They Were ONLY Selling 11 Hours Per Week! | Donald C. Kelly - 1997
Salesforce found that reps spend just 11 hours per week actually selling. That means nearly 70% of their time is spent on everything else. So where is it going? Let’s break down what sellers are really doing and why it’s keeping them from hitting quota.Identifying Time-Bleeding TasksLet me show you what’s really taking up their day. A lot of it comes down to necessary work that just takes way too long. Think about the time spent digging for information before a call. That can easily turn into 45 minutes of manual research for one prospect.Then there’s building proposals and assessments. Reps are sitting there formatting documents, choosing layouts, and putting together decks when that time could be spent in front of a customer.On top of that, you’ve got CRM updates, data entry, and internal meetings that keep pulling reps away from actual selling. It all adds up fast, and before you know it, the day is gone without much time spent with buyers.Leveraging AI and Process OptimizationSo how do you fix it? It starts with getting rid of the work that does not need to be done manually.AI is making that a lot easier. Instead of spending close to an hour researching a prospect, reps can pull together key insights in just minutes. CRM updates can be automated. Meeting notes can be summarized without lifting a finger.And when it comes to proposals and documents, this is where better systems come in. Instead of starting from scratch every time, teams can use templates or even hand off parts of the process so reps can stay focused on selling.The goal here is simple. Take as much off the rep’s plate as possible so they can spend more time doing the one thing that actually drives results.Actionable Steps for Leaders and RepsIf you want to fix this, both leaders and reps have to take a hard look at how time is being used.Start by tracking it. Spend a week writing down exactly where your time goes. Prospecting, emails, research, meetings. When you see it on paper, it becomes a lot clearer where the gaps are.From there, leaders need to step in and protect selling time. That means cutting back on unnecessary meetings and making sure reps have systems that actually support them.And finally, simplify the tools. When everything is scattered across different platforms, it slows everyone down. Bringing those tools into one place makes it easier to work faster and stay organized.At the end of the day, this is about making sure your reps are spending more time in front of customers and less time stuck in the background work.“Time is ticking and time is money.” - Donald C. KellyResourcesKeep track of your sales activity and boost your results with the Prospect Pro sales tool.Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.Visit Blue Mango Studios for help in creating podcast production content.Sponsorship OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by LinkedIn.Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.CreditsAs one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: <a href="http://thesalesevangelist.com/survey" rel="noopener noreferrer" target="
- 3 weeks ago13 min
Missed Quota Series: The AI Gap is Real...You Debate "It's A Fad, While Your Competitor Is 6 Months Ahead of Your | Donald C. Kelly - 1996
Salesforce found that sellers who use AI are 3.7 times more likely to hit quota. So what are they doing differently? Let’s break down how AI is helping sellers work more effectively and why it’s becoming a core part of modern sales.Maximizing Efficiency in Prep and ProspectingAI is taking a lot of the busy work off a seller’s plate, especially when it comes to prep and prospecting.Instead of spending 45 minutes digging into a single prospect, sellers can now pull together key insights in just minutes using tools like ChatGPT or Claude. That kind of time savings adds up fast.And it changes how sellers spend their day. When you’re saving 30 minutes or more per prospect, that time can go back into higher-value activities like engaging on LinkedIn or actually reaching out to prospects.AI is also making personalization easier to scale. Sellers can quickly find relevant details about a prospect and use that information to craft more thoughtful, tailored outreach without starting from scratch every time.AI as a Sales CoachAI is not just helping with research. It’s starting to act like a built-in sales coach throughout the deal cycle.Sellers can use it to think through different scenarios before a call ever happens. By plugging in meeting notes or past conversations, AI can highlight potential risks and help them prepare more effectively for discovery.It’s also useful when it comes to handling objections. Instead of guessing how to respond, sellers can use AI to brainstorm different approaches, especially when they’re up against a specific competitor.And before a deal moves forward, AI can help pressure test it. Sellers can ask it to find gaps, weak points, or anything they may have missed so they can tighten their approach before presenting a solution."You're shrinking the busy work so you can focus more on selling." - Donald C. KellyResourcesKeep track of your sales activity and boost your results with the Prospect Pro sales tool.Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.Visit Blue Mango Studios for help in creating podcast production content.Sponsorship OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by LinkedIn.Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.CreditsAs one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or <a href="https://open.spotify.com/show/1NjzsFjQwVrgboUfDvbzd5?si=LdQOJDc1T-WB
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About The Sales Evangelist
I believe in doing BIG THINGS! You should be earning 6 figures easily as a sales rep. But chances are you are not...yet! Sales is the most important department in every company but many sellers are never taught how to effectively sell, much less how to earn their way to high-income status. My own career limped along until a company I worked for invested in sales training to help me succeed. Immediately afterward, I closed a deal worth 4X what the company spent on me and saw hockey-stick improvement in my performance. So I started a podcast to “Evangelize” what was working. Today I interview the world's best sales experts, successful sellers, sales leaders and entrepreneurs who share their strategies to succeed in sales right now: folks like Jeffrey Gitomer, Jill Konrath, Bob Burg, and Guy Kawasaki to name a few. They share actionable insights and stories that will encourage, challenge, and motivate you to hustle your way to top income status. If you’re someone looking to take o
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