There's a few different ways to gauge a candidate's autonomy in a sales interview. 1. Behavioral Questions: Ask situational questions that require candidates to describe times where they had to work independently to achieve sales targets or overcome challenges. For example one of my go to questions is, "What's the most creative, out of the ordinary, or above and beyond thing you’ve done to win a customer?" 2. Past Experience: Review the candidate's resume and ask about specific examples where they demonstrated autonomy in previous sales roles. Inquire about their sales process, strategies they implemented independently, and decisions they made autonomously. 3. Problem-solving Scenarios: Present examples of current sales scenarios and ask how the candidate would approach them. Evaluate whether they demonstrate the ability to think critically and make decisions independently in real life situations that arise. 4. Role-play Exercises: Conduct role-playing exercises where the candidate must handle a sales scenario independently. We ask candidates to run a discovery call and give them basic information on the team. Observe how they handle the situation and objections without much assistance or input.

Staying up to date: It’s important to pick a medium that you like for content. Whether it is Linkedin, podcasts, email newsletter, or chat based slack groups, you want to make sure you are setting yourself up for success. If the content goes unread or unlistened to, you won’t build a consistent learning habit. Personally, I find the most value in content forums where you can engage and ask follow up questions, hear multiple opinions on a particular matter, and even reach out the the original writer for a 1-1 chat! Another underutilized source of knowledge for industry trends is content from Sales Development technology vendors. It’s imperative that they stay on the cutting edge, so following a few top vendors on Linkedin will allow you to see what future the tools are preparing for. Avoiding the noise: There can be a great amount of value in public best practices. That said, there is risk in assuming that something that works for someone else will also work for you, or for implementing changes to something when you are already seeing above-average results. For example, if your content is getting a 20% reply rate, you may not want to adopt the “best practice” that moved someone else's team from a 10% to 15% reply rate. Having your own benchmarks and running your own A/B tests can help you determine where you should be altering your SDR motion, and where you should keep yours in place. Then, you can proactively search for interesting ideas to test in areas you are performing below benchmark. 

The answer to this question depends on the sales leader (i.e. me vs someone else), the product that the rep is selling, the stage of the business, etc. The list goes on. I personally am always looking for candidates who have these two attributes: 1. Innate curiosity 2. Persuasiveness The first is (hopefully) obviously critical. The more curious the rep, the better they should be at discovery. The better they are at discovery, the more time you can spend helping them execute the back half of their deals. The second is also hopefully obvious. I know plenty of reps who excel in sales through discipline and structure, but I'd take a rep who is also persuasive (on top of those things) any day of the week.

Since nearly everything is quantified in sales, OKR's can sometimes come across as redundant and inconvenient to manage to the uninitiated. But OKR's are an amazing vehicle to drive focus on the core strategic initiatives that will generate greater success, and gain cross-functional alignment, visibility and support in achieving these goals. There are two major benefits IMO opinion in defining Sales OKR's: 1. Clarity - the process of defining Objectives and Key Results, if applied with rigor and assistance from someone truly knowledgeable in the process, can provide immense clarity into what you're looking to achieve and how to achieve it. The question was about the output, but let's not overlook how valuable the process can be to get really crystal clear on the Objectives that will have an outsized impact on team results. 2. Cross-functional alignment - OKR's are a company initiative, not a Sales initiative. This means it's a common language across departments, that can be used to unite teams in a shared mission, and increase visibility in what other departments can do to help each other out in achieving their objectives. There are few other tools that are as impactful as a supporting team attached to one of your KR's having to read out progress each week to their leadership. Every sales person wants more support from the company to sell. If it's possible to define exactly what that support is, who it's from , and tie it to a KR... drumroll please... you just got the support you needed via OKR's! So what defines good Sales OKR's? First step is in accurately defining the highest priority Objectives, that if achieved, would have a greater impact on Sales than anything else this quarter. A couple nuances to address: 1. Typically there are top line company objectives that are rolled out first, and then all departments (including Sales) localize their objectives to support some or all of the overall company objective. This is important to call out, as this exercise of connecting Sales goals to Company goals helps define the focus of OKR's. 2. The localizing of company objectives should generally just change the wording of the Objectives to ensure they align, but the big rocks that sales should focus on are typically in the following categories * Building a High Performance Sales Culture (hiring, ramping, setting a high bar for execution, focus on improvement of the culture) * Building Pipeline * Deal Execution - win rate, competitive win rate, utilizing resources more effectively to improve results, closing bigger deals/more deals * Executing new strategies to increase deal size, improve velocity, or open up new markets to increase TAM. Under those big rocks, you'll need to define the KR's that get you there. They need to be measurable, a stretch but achievable, and simple to track. This is harder than it sounds - but the process of refining these helps you gain that clarity. This is where you can really lean into intentionally setting up cross-functional goals, and align the support of the company to help Sales achieve their Objectives. A few examples: * If the goal is getting more customers in an industry - one KR could be to sign up 3 current referenceable customers for case studies. This aligns sales and marketing to build assets so you have more stories and social proof to help you sell into this industry. You could then have an additional KR on how many net new customers you are closing that quarter in that industry. * If you're looking to increase ACV as part of a Deal Execution objective, often there is a KR related to selling add-on products. You could align with the Product & Solutions Engineering teams to produce more assets, custom demo environments, or a new Guru card to improve sales' ability to sell this feature. Paired with an attach rate goal, this can be a powerful combo. * If there is a Culture objective, and you have a Culture survey in your org, addressing one of the key items that has been flagged by the team is a great way to show commitment towards improving the environment. For example there could be a new tool that addresses a major gap or point of friction for AE's. Setting roll out dates with RevOps that map to improved productivity is motivating to the team. While every company is different, sales Objectives are going to generally fall into one of 4 major categories outlined above. These need to be mapped to the company Objectives, and then it's important to lean into the benefits that the OKR process provides when defining KR's. Clarity in how to hit your Objectives. Visibility across the org of the key strategies you're leaning into the hit your Objectives. Cross-Functional alignment to get all teams rowing in the same direction to achieve shared Objectives.

I don't have a favorite question but I do prefer open ended questions in discovery. Close ended questions start with helper verbs. Every question beginning with these words(Am, Are, Is, Was, Were) can be answered by a buyer with a yes or a no. Even when folks give you more than a yes or no they will always be giving you less than a response to an open ended question. To get the most information and provoke deep thought from a prospect. I coach my team to leverage open and command open questions. For example questions that start with Who, What, Where, Why, Tell Me, Explain, Describe, Help me understand ETC. When you construct questions that are "open ended" buyers will elaborate and provide answers with a lot of detail.

Our top reps excel at spotting potential opportunities. Since we're focused on run-rate tactical deals in the form of additional license, new initiatives, and pilots, our main stakeholders are typically at the VP level or below. The key here is mastering the art of tailoring conversations - distinguishing between "above the line" and "below the line" discussions ensures that our messaging aligns with the audience. In larger enterprises, industry trends and company direction are often widely available. It's crucial to delve into these trends, gaining a deep understanding of industry challenges and directions. This forms the basis for crafting a unique perspective that resonates not only with the business but also its key players. Once everyone's on the same page and the problem is crystal clear, we can then propose a forward-thinking solution that drives them towards their desired outcomes. What sets this approach apart is its emphasis on discovery. Rather than leading with a product pitch, we invest time in understanding the company's priorities. This makes our interactions much more aligned with the client's needs, creating a more genuine and less "sales-y" experience. This method ensures that our solutions aren't just one-size-fits-all, but tailored to fit the precise needs of each client we engage with.

I think there’s a lot to be said about optimizing sales processes with AI. As software continues to improve this will allow AEs to be more productive, manage larger books of business, and deliver highly customized outbound messaging. That said, given the sheer volume of outreach prospects receive today, it’s more important than ever to differentiate yourself, build your network, and establish yourself as a thought leader in your space. If I were an AE starting today, I’d focus on what I want to specialize in and start building relationships—not just with prospects and customers but also with partners in the ecosystem.

During your Q4 working with sales leaders and operations your sales kick off should be the launch pad for your sales content and strategy for the year by supporting the company revenue goals and big bets for that year. What I have found to be very successful by conducting quarterly enablement reviews sales leaders and their direct reports. The framework for these meetings is to review the performance of enablement and allows time to review metrics and showcase data insights from those metrics. What is uncovered in these meetings will help you to develop new sales content and build a mutual strategy with your sales leaders. This is also time to present any new programs you want to get sales leaders buy in from prior to launch.

There is a give and take with standardizing KPIs but also having enough variance to account for things segment, (Strat, Ent, MM, Growth) number of accounts, and so on. The easiest way to have consistency and also provide a lens to inspect forecast is by implementing standardization when possible. No matter what segment you're in or how many accounts you have, if a deal is 345 days old... that's going to tell me something about the forecast accuracy of the stage it's in. I am a big fan of ensuring reps are training that in the mid point of the quarter or month, whatever your quota and cadence is, deals with a close date in quarter or in month must be in Best Case, Commit, or Closed. Nothing can be in "Pipeline" or "Omitted"

In my experience, communicating the performance & progress of your sales team to the company helps to connect all employees to the mission. It can create transparency into the health of the business, aligns individuals within the company more closely to the voice of the customer, and enables you to more easily activate resources when support is needed. On a Daily Basis... * Every time a deal is Closed/Won, a "Congratulations" email is sent out to the whole company, and a Slack message is posted in our "team" channel sharing the details of the deal & the "Win Notes" (ex. the customer, the value of the deal, the "why" behind their purchase, any learnings, and shout-outs to teammates who helped to close the deal) * For the biggest deals or most special wins, I'll also create fun memes showcasing the rep & the customer and share that via Slack & email too On a Weekly Basis... * I'll create a Freehand with 4-5 slides sharing our progress (Closed/Won against Target, Pipeline Generation over the last week, etc.), shouting out the biggest & most prominent deals of the week, and sharing the most relevant & interesting customer stories. Then I'll record a 3-4 minute video walking through the content, adding my commentary & perspective, and then I'll share the video & the Freehand in our "team" Slack channel so everyone in the company can watch it & engage with the content * I also look for opportunities and encourage my sales managers & sales reps to post in our "sales" Slack channel any interesting stories or learnings throughout the week. Sharing snippets from chorus calls, best practices for generating conversations or overcoming objections, and capturing the greatest success stories helps to raise the overall knowledge of the organization. On a Monthly Basis... * During our company All-Hands, I'll provide and expanded version of my weekly Freehand & video, and also look to provide the platform for 2-3 of our sales reps partnered with their account or customer success managers across different segments/regions to share their customer stories with the entire company. And keep in mind...it's as important to celebrate the journey just as much as the wins, especially if you're in an earlier stage organization. Communicating the behaviors, the mistakes, the learnings, and the process behind your sales motion is often even more valuable for your entire organization than the wins alone.