In order to get a better understanding of what you could be walking into, I suggest asking the question "What is your biggest problem and can I help solve it?" It shows genuine interest in the interviewer's pains/goals and enables you to see how you can make an impact. Aside from this key question, always make sure to check out these resources before stepping into the interview. 1. Company Website: Familiarize yourself with the company's products or services, mission, values, financials and recent announcements. 2. LinkedIn: Research the hiring manager and other key stakeholders to gain insights into their backgrounds and professional interests. 3. Glassdoor or RepVue: Read reviews from current or former employees to learn about the company culture, interview process, and potential interview questions.

I really like this question because it's so true! Leadership can break a lot of trust by implementing incorrect KPIs for a segment. Experienced sellers will get angry they are treated like SDRs, etc. The best thing leaders can do is watch, listen, observe, and then replicate. What have the most successful reps done in this position? Are they having 10 calls a week, 2 on-sites a month, and 1 "high value activity" a quarter (like exec intro, hackathon, etc)? Standardize from the top and make excellence the norm.

Must-Have Sales Leader Hard Skills: * Data Analysis and Decision Making * Decisions can't be made on a whim-they need to be based on data * You need to be able to analyze data to understand the health of your business and the businesses of those who report to you * You need to be able to pull key insights from data to drive strategy and as a way to get your team bought into executing on the strategy you set * Communication Skills * With customers, other leaders, cross-functional partners, and reps * You need to be comfortable having tough conversations when necessary * You need to inspire your team to take action and execute * Time Management * Time is limited- you need to understand how to maximize it, free it up (delegate), and prioritize/deprioritize * Negotiation Skills * Not just with customers, but internally with cross functional partners and key stakeholders in order to get things accomplished within the business

Building a framework for measuring and managing soft skills is challenging but achievable by focusing on qualitative and quantitative metrics. Here’s how you can build a manageable framework: 1. Define Key Soft Skills Relevant to the Role • Identify the most critical soft skills for success in your sales environment. Examples might include: • Emotional Intelligence • Communication Skills • Active Listening • Problem-Solving • Adaptability • Collaboration 2. Set Clear, Observable Behaviors • Translate each soft skill into clear, observable actions. For example: • Emotional Intelligence: How well does the rep manage stress and handle rejection? Do they adjust their approach based on the customer’s emotional state? • Communication: Is the rep able to convey ideas clearly, concisely, and persuasively? Do they actively listen to customers’ needs before responding? 3. Establish Quantifiable Metrics • Use a combination of self-assessment, peer feedback, and customer feedback, coupled with performance data. Examples include: • Customer Satisfaction Scores (CSAT): Measure customer feedback related to interpersonal interactions. • Peer Review or 360-Degree Feedback: Incorporate feedback from managers, colleagues, and cross-functional teams on a rep’s collaboration, communication, and adaptability. • Sales Cycle Time: Track how quickly reps can navigate complex conversations or objections (communication & problem-solving). • NPS or Client Retention: Measure long-term relationship-building (empathy & emotional intelligence). 4. Incorporate Qualitative Feedback • Gather qualitative data from customer comments, peer observations, and manager coaching sessions. Use structured questions like: • How did the rep handle objections? • Did the rep demonstrate empathy during the sales process? • How well did the rep adapt to changing customer needs? 5. Create a Rating Scale • Develop a simple rating scale (1 to 5) for each soft skill, aligned to the observable behaviors. This could look like: • 1: Needs Improvement • 3: Meets Expectations • 5: Exceeds Expectations For example, for Active Listening: • 1: Interrupts customers frequently and fails to address their pain points. • 3: Allows customers to fully explain their situation and responds thoughtfully. • 5: Proactively asks clarifying questions and tailors the solution perfectly to the customer’s needs. 6. Monitor and Coach Regularly • Build these metrics into regular performance reviews and coaching sessions. Use them as discussion points for ongoing development rather than just static evaluations. • Sales role-playing or shadowing can help assess how reps apply soft skills in real-life or simulated scenarios. 7. Set Improvement Goals • For each soft skill, set specific, actionable goals. For example: • Improve customer satisfaction by practicing active listening techniques during calls. • Increase adaptability by training reps on handling complex objections in varied industries. 8. Benchmark and Track Progress • Set baseline scores for each skill and track progress over time. This helps you see where improvement is happening and where additional coaching might be needed. 9. Leverage Technology • Use tools like CRM data to track certain soft skill outcomes (e.g., client satisfaction, deal velocity) and integrate them with feedback systems like surveys or peer reviews to have a centralized platform for measurement. Conclusion: By focusing on specific behaviors, using a mix of qualitative feedback and quantifiable metrics, and regularly tracking progress, you can build a manageable and actionable framework to measure and develop soft skills in your sales team.

Sales stakeholders can come from any department within an organization and as the company grows, their input is key to sales success. A few examples may be: 1. Product Teams: aligning sales strategies with new offerings and/or customer feedback 2. Marketing: greater integration for cohesive messaging and lead gen 3. Customer success: ensuring client satisfaction and retention 4. External partners: distributors, resellers, support partners can help expand market reach The best method to building and maintaining relationships with your stakeholders is to regularly communicate with them. Show appreciation for their support, inform them of changes, address their concerns and involve them in key decisions that may impact their area of the business. Creating trust and consistent communication will help build, or strengthen, your relationships.

The most important intangible traits for account executives include a strong willingness to learn, grit, and the ability to build meaningful relationships while earning clients' trust. They should position themselves as thought leaders in their industry and be genuinely passionate about what they sell, as this authenticity drives success. On the tactical side, organization is the most critical skill. Account executives who manage their book of business with structure, clarity, and a sense of ownership—treating it as if it were their own company—are far more likely to be successful.

While tech may have downsized lately, great sales professionals still have lots of options. The major driver of recent layoffs were to create more efficiencies in businesses; which leads to lower burn and more profitability. There are few roles as efficient and impactful on profitability as a top seller exceeding their quota. By nature these folks will always be sought after and have options - so retaining top talent should always be a priority. The biggest mistake I see in retaining talent, is front-line managers DAM'ing their team. They only manage: D- Deals - when the deals are there and closing life is good! When they're not, the only lever they have is to drive activity. A - Activity - when deals are there, activity check-in's are infrequent and leading indicators of poor future pipe are missed. Once the pipe dries up, poor managers micro-manage activity and ramp up the urgency on activity without offering much actual guidance on how to drive better conversions. "Do more" is the mantra. M - Morale - any decent manager is going to check-in with their team. If they aren't truly helping their AE be successful then morale will probably be good when they're winning, and lower when they're not. Especially low when they're being micro-managed for prospecting... Now let's compare this and understand why a top performer would stay in the first place. There are 4 core reasons and an elusive and fleeting 5th reason. 1. They feel successful, are making money, and feel they're being fairly rewarded for their work. 2. They're developing skills and growing. They know that the hard work they put in today will pay dividends down the road. 3. They see opportunities for career progression and advancement. They believe there is opportunity to get promoted, or take on meaningful work that would represent professional growth, in an acceptable timeframe. 4. They're having fun and/or enjoy the people they work with & for. If you hit all 4 of these and/or if you are a part of a very mission-driven organization with inspirational leadership, you can tap into the 5th category: 5. They feel like they're a part of something bigger than themselves. This last one is a by-product of doing a lot of other things right. But if you can reach that pinnacle - this issue will take care of itself. Now if we apply the DAM method to why people would stay: 1. If the deals are there, the DAM Manager would theoretically focus on and help the AE close their deals. When pipeline is present the DAM method can work. Of course if it's not - this is strike 1. 2. Outside of situational deal coaching, there's no skills development carved out in the DAM method 3. Promotions are a by-product of hitting your number or not 4. It's fun when you're winning and unless you're on a great team, you don't really enjoy where you work when you're in a slump. A normal person needs 3-4 to feel good about where they work, 2 to be okay with it, and 1 to begrudgingly stick around. Literally everything above is dependent on there being enough pipeline and the AE closing deals. There is absolutely no reason for someone to push through to the other side when things get difficult. This is what causes someone to hit the bare minimum of requirements and demand a raise or promotion. They aren't having fun (4), they're not developing skills (2), they aren't making the money they want to make (1), so the only way to justify their existence is to get promoted (3) - which will give them fleeting relief until they move on 6 months later after the other 3 don't change and the next promo is 2 years down the road. So what DO you do: 1. Everything is easier when you're winning. I'm not going to break this down too deep - but more people feeling successful, hitting quota, making money, setting records, the more they'll want to stick around and keep doing it. Also check quotas to ensure they're realistic, attainable and surpassable. Make sure comp is competitive and I'm a big fan of accelerators to ensure your most talented AE's put the hammer down after they've hit quota instead of backing off. You can also get creative and make the highs higher. President's Club produces so many memories and is a silent motivator throughout the year. Hi-Po dinners or events for top performers throughout the year are another worthy investment. Once you've had a taste of being in the exclusive club for top performers you never want to back. 2. Working on Skills Development is where I think most companies can improve their standing with talent. Learning slowed down when we went remote. You used to have to be less intentional, and the osmosis of hearing everyone do the job, or being able to ask your neighbor a question, improved skills naturally. This has dropped off a cliff. According to the Bridge Group, ramp time now sits at 5.7 months compared to 4.3 months in 2020. This is an industry wide problem. While you can (and should) analyze your onboarding program, possibly hire outside training for a shot of adrenaline, and look at your enablement team for help here - it's not all on enablement. The gap is more on day to day coaching. Leaning in and investing in your front line leaders to be better coaches and develop THEIR skills to uplevel the AE's skills is where you'll have the biggest impact in my opinion. The bar for this also gets higher as the AE gets more talented, so it's important that front line leaders can not just coach the basics, but can help talent get to the next level. "Coaching" or "skills development" in general however just doesn't take up much real estate on enough managers' calendars. 3. Upward mobility is another silent motivator that drives people to keep working hard in the background. If your most talented people have reached the highest rung - you should identify this as a risk and think through if there are opportunities to create a new promotion level, carve out more responsibility, or add a rung to the ladder in some way. I've interviewed so many AE's who were talking to me because they felt "they had learned everything they can at their current company." Don't ever let that be the case, or don't be surprised when they leave. One thing I undervalued coming up as a leader was clarity of promotion path. I thought it was obvious that if you performed at an elite level, you would be in the conversation for a promotion. Some people can put their head down and operate at their best under these guidelines, but you miss your core performers. Core performers hate this answer, and by getting more clarity around the exact expectations for a promotion, you can often get more out of these folks as they work towards checking off all the boxes. I have also tried to talk talented people off a ledge who felt like it just wasn't clear how they get to the next level. We need to know that taking a new job, with a new title, at a new salary, is always crystal clear. So if someone is in their office at home, thinking through their next couple of years - if they can't see how they would move up in your organization, it's going to be a lot easaier to believe their easiest path is to go somewhere else. Change this, and prove it. It's so important to show promotions and ensure everyone knows those stories - what they did, how they did it, and how "you too can get those same results." 4. In a remote world "fun" is a lot harder to come by. I used to love coming to the office. My teams typically loved it too. We had a great group of people that genuinely enjoyed working together for the most part. Energy was through the roof. We had tunes going, people on the phone, we celebrated everything, gongs were ringing, jokes were made on the floor, deals were broken out live, people were learning, succeeding and had camaraderie around them to push through it if they weren't. We'd go out together from time to time and we made work fun. That is just near impossible to replicate in a remote world (if you have the secret sauce DM me!). What you can focus on however is building culture. Putting together an intentional team that wants to lean in, engage, and work together in this new capacity. Create opportunities to collaborate, learn and grow together. Anoint members of your team who have a pulse on the rest of the team to step up and help drive this so it lands. They can fill your blindspots. Invest in getting people in office whenever you can. If someone really likes their boss, this can make a huge difference too. Ensure your front line leaders are a big plus in this column. Which leads us to number 5 5. While a lot of things need to click for the team to feel like they're a "part of something bigger than themselves" there's one quality that will keep people around well beyond the point of logic, and help create a dedicated army for the cause. Inspirational leadership. You can find this at all levels - however you've heard about an inspirational leader behind many of the world's most iconic runs. Tesla had Elon Musk. Apple had Steve Jobs. Yammer had David Sachs. Hubspot had Brian Halligan. OpenAI was about to lose the whole company when they tried to oust Sam Altman. People will follow inspirational leadership through hell and come out the otherside unscathed and still committed. It doesn't need to be a silicon valley legend however. There are inspirational managers, directors, VP's and team leads across the industry. I feel this is undervalued however. If talent is really thinking about leaving - are they inspired? Are you inspiring them? If this feels like a gap - start with clarity of the Mission. What hill are we taking, what's our goal - beyond just hitting revenue targets. What's the strategy for hitting that goal? Why does that matter for the team? What's in it for them? Why are they lucky, one of the chosen few, to be on that mission here and now? If you can answer all of those things - people are probably inspired. If not - it mght be a good exercise. I map all of this out in detail to provide the ability to audit your own org, or an individual. You would love to answer yes to all 5, but identifying where the no's are can give you a clear roadmap on what to fix to systematically retain talent. 1. Do they feel successful, are making money, and feel they're being fairly rewarded for their work? 2. Are they developing skills and growing? Do they know that the hard work they put in today will pay dividends down the road? 3. Do they see opportunities for career progression and advancement? Do they believe there is opportunity to get promoted, or take on meaningful work that would represent professional growth, in an acceptable timeframe? 4. Are they having fun and/or enjoy the people they work with & for? 5. Do they feel they're a part of something greater than themselves?

Over-indexing on trying to look good by manipulating the narrative or masking challenges or flaws. Better to be honest and proactive where there are challenges, especially if it is you that has not done well enough to deliver against what is needed. Radical candor is/was talked about a lot but no matter how much practice you get the reality is it is hardest to deliver the truth when it is often most important to do so. My very first forecast call with a new CRO I was nearly certain would cost me my job. Instead, I think in part because of my honesty and directness (the news I was delivering was not good!) it turned into a pretty pivotal moment for me and my team as a result.

Very interesting question — and one that brings up a few more! * Quota attainment is a KPI that is directly meaningful to a seller—if she can hit her KPI of quota attainment year after year, that will be meaningful to her personally! * However, quota attainment isn’t a helpful KPI to the company by itself — we could find out that the above seller is selling bad deals — selling deals that have low margins, high churn rates, and more… This is why it’s important to have a several KPIs that are developed to the needs of the business—and to the needs of the seller. Otherwise, it’s like judging someone’s safe driving ability solely by whether or not they drive the speed limit. Many people drive the speed limit, but are looking at their phone, or are ignoring their turn signals, etc. It’s one KPI that will help inform whether a driver is safe, but it’s not the only way of determining whether a driver is safe.

I am so glad you asked this question - discovery and storytelling is such a huge passion of mine, so happy to share my perspective: Best Practices I See From Top-Performing Sellers 1. Deep Discovery During Every Interaction – High performers never stop doing discovery - every conversation is an opportunity to learn more from your prospects/customers. While doing discovery, they don’t just ask closed ended (yes/no) questions, instead they focus on open-ended questioning (e.g., “Can you tell me more about that?” or “What happens if this problem isn’t solved?”). They uncover not just pain points but the underlying business drivers. 2. Structured and Flexible Approach – They follow a repeatable discovery framework but remain flexible, adjusting based on the conversation rather than checking boxes. 3. Active Listening & Strategic Note-Taking – Instead of rushing to pitch, they actively listen to their audience, ensure they summarize key points, and document these insights that allow for them to reference in future conversations (e.g., using Gong or CRM notes to track recurring themes). 4. Customer-Centric Positioning – Sellers will then translate what they learn into highly relevant recommendations, aligning their messaging with the prospect’s specific needs instead of delivering generic value props. 5. Multi-Threading Early – Top sellers engage multiple stakeholders early, and often, ensuring broader buy-in and reducing the risk of deals stalling due to a single point of contact.