1. Tell me about a deal that you were particularly proud of closing. How did you overcome obstacles to secure the deal? Proper Answer: The candidate should describe a specific sales challenge they faced, such as a tough negotiation or a difficult client objection. They should then explain the strategies they used to overcome the obstacle, such as active listening and creative problem-solving. 2. Tell me about the most challenging part of your current role and how you’ve overcome or mastered it. Proper answer: We’re looking to see an answer representative of a growth mindset. We want to hear examples of the individual overcoming adversity and sharing how they adapt and evolve in the face of challenges. 3. Tell me about a time when you received negative/constructive feedback from your manager, how you respond? Proper answer: This question aligns to the value of “learning faster through feedback”. How did the individual respond to the feedback and implement action (if any) in order to develop. 4. Explain concisely how your company creates value for customers. Proper answer: We’re looking to see if the individual can provide a short, easy to understand and memorable description of the product or solution. This is an indicator of strong communication skills. 5. Tell me about an opportunity that you lost that really hit hard. What did you learn? Proper answer: The answer should illustrate humility and resilience. Did they learn what to do next time to ensure a better outcome? Do they have an example of implementing the learnings?

I like a consistent review of competitive win rates by stage. I think these can serve as early signals to so much: from how your narrative is landing, whether price is where you fall down or perhaps even foresight into late losses building up as a result of a missing piece of functionality or two. We have the benefit of someone who dedicates the majority of their time on content creation, visiting with customers and regular analysis of our results. Whether or not you can make this a full-time job, I think carving it out intentionally for a relevant function to own is worth it - the insight is invaluable.

Firstly, it is important to recognize that discovery is not one stage of a sales process nor is it only the questioning that occurs on your first meeting. Discovery is a continuous journey of leading with curiosity, probing deeper, summarizing your understanding, and validating your takeaways through the sales process and with each new individual in the sales process. To ensure your discovery is efficient & effective... * Do Your Research & Prepare: the better you prepare for the conversation and align on the answers you need to best identify if/how your solution may be of value to the prospective customer the more effective you'll be able to use your time * Stay Curious: if you engage in curious, open-ended questions you will be able to uncover more critical information than if you focus on a standard set of pre-defined & closed questions * Probe Deeper: don't take just the surface level answer to questions, keep digging deeper to get to the root of their current state, goals, challenges, pain, etc. * Summarize & Validate Your Understanding: always make sure to summarize what you heard and validate you heard that correctly. Ultimately, the underlying business case is your prospective customer's story in their own words, so while you can craft it through discovery, to align on the true narrative, it needs to be in their words. If through your conversations you cannot get the prospective customer to articulate 1) why they need to do anything, 2) why they need to do it now, and 3) why your product is the best solution, then that may indicate you have sufficient holes in your deal which could require you qualifying out.

I don’t believe there’s a single "right" career path for a sales professional. Sales is an incredible foundation that can lead to countless opportunities because the skills are universally valuable. Whether you’re pitching investors as a founder or advocating for an internal business initiative, you’re always selling—yourself, your ideas, your vision, or your work. Traditionally, Sales careers may start as an SDR, progress to AE, Mid-Market AE, Enterprise AE, and eventually to Client partner or Senior Relationship Manager. Alternatively, you might take the leadership path, from sales manager and graduate to senior leadership roles. Ultimately, your path should align with your strengths and what gets you excited every morning.

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?

I alluded to this in an earlier question, there will also be those KPIs that come as "standard" to the sales job. How many calls did you have in a week, how many discovery calls vs demo calls, etc. However, what I pay most attention to is what KPIs do top sellers consistently hit? Do they do more in-person meetings? Do they leverage Executives more? How often do they expand into another business unit in an org? I map out KPIs based on top performers and hold reps accountable to that activity.

Oftentimes, conflict exists because we aren't listening or are unwilling to consider another person's perspective. I've found the best way to resolve conflict between team members is to actively listen to understand each party's viewpoint while remaining neutral to avoid taking sides, and encourage communication to find common ground or goal. You may find the right answer lies somewhere in the middle of both parties.

Quarterly and annual OKR's on an individual level need to be broken down from the Company/Segment/Team Level. Once the overall priorities are defined you can identify the contribution on the individual level. I would say to define projects based on the gaps you are seeing and cascade them down to the individual level. Ultimately, the sales goal will be defined by the revenue goal broken down by segment and product. The expected growth rate will determine the priorities. Will the growth come from productivity increase per rep or by headcount growth? Do you have a Total addressable market (TAM) constraint? If yes, how can you increase that? Once those types of questions are answered the goal will be to monitor progress based on KPIs. Most importantly, Revenue, Pipeline and Activities (the order matters!) If Revenue and pipeline is in good order activities become less of an issue. If not, activities need to be looked at to build enough pipeline to reach revenue targets!

Here are some of my tips on how to qualify an internal customer champion A true champion should have: 1. Influence – Can they drive internal conversations and decisions? 2. Access – Do they have direct connections to decision-makers? 3. Advocacy – Are they invested in your solution and willing to push for it when you are not in the room? 4. Knowledge – Do they understand the business problem and see your solution as the answer? To validate potential champions, ask questions like: • “Who else needs to be involved in this decision?” • “How have similar decisions been made in the past?” • “What challenges could come up internally, and how can we address them together?” If They’re Not a Strong Champion • Ask for Introductions – Position it as bringing in the right expertise: • “To make sure this aligns with your company’s goals, who else should we loop in?” • Grow the army – Offer resources that help them build internal buy-in. • Leverage Leadership – If you have a senior contact, use them to request an intro from the top down. If they resist, they may not be fully bought in—keep testing their commitment before investing too much.

Good question. I have seen these people in my time as a leader as well. However, not all sellers fall in to this bucket, so KPIs should be in place to support the rest of the team and encourage consistent behaviors. I have seen sellers that are more junior in their sales career or new to a business ask for KPIs (reflective of the top sales performers within the team) so that they can add more structure to their day/week and help them formulate a plan that will eventually get them to a positive quota outcome.