What are some questions you need to ask when interviewing executives for sales leadership positions?

2.1k views2 Upvotes7 Comments

Director of Sales in Retail, 51 - 200 employees
How do you intergrade analytics with the human factor for a sales team?  How adaptable are you with your training methods for a sales team and on the individual level?  What is your vision for this role and how do you plan on achieving that vision?
CEO in Hardware, Self-employed
Explain your leadership style to me...
Given the following three competencies - industry knowledge, business acumen, and product knowledge - which is the most important for your sellers to have, and why?
Explain to me the difference between managing and leading... 
Founder and Chief Sales Energizer in Services (non-Government), 2 - 10 employees
What criteria will you use to make the decision about whether this is the right position for you?

Give me an example of a time when you had to manager your manager?

How do  you determine what a salesperson needs to be coached on?
Founder in Services (non-Government), Self-employed
This is arguably the most important position in your company if you are looking grow revenue. So please forgive the long answer here. The right person leads your organization down the path of record breaking growth that investors and stockholders look for. The wrong person results in a culture of under performance, excuses, and churn (both in salespeople and customers).

Because it is so critical, I recommend first determining the requirements of the role to be successful, which will largely depend on what stage your sales organization is at. Are you a startup adding product lines, establishing a brand and market presence, hiring sales people as fast as you can? Are you getting competition pressure and need to differentiate yourself? Or perhaps you’ve won the battle and need to maintain your position and standing. Maybe you have been around for a while and are seeing increasingly diminished returns and need to clean house a bit...

And while each stage requires a different skill set in the executive you hire, whether you're a startup or an established small company looking for accelerated growth, or if you have new division or a territory that is under performing, they have the daunting task of building a sales model, recruiting (or culling) a team, and personally developing that team.

Here are my go to questions in 8 critical areas that I look for them to offer examples of:

Leadership style: Do they focus on their ability to lead, or their team’s ability to follow? What do they do when their strategies do not align with others, can they still get to the desired outcome and consistent results? How do they make decisions; top down, bottom up, or a combination? Do they take strategic actions to achieve a written and shared goal, or act for the sake of action? How do they prioritize time on the team (not in it)?

Strategic thinking: How will they focus on the right issues, not the most urgent ones demanding their attention? What would their first 90 days look like? How will they  adopt best practices in the areas that are in need of improvement? How do they determine what needs improvement? What is their approach to change and problem solving? How resilient are they in the face of failure?

Relationship building: Will they spend time in the field with both their managers and reps? How do they handle managers who are upset? Will they spend time building relationships?

Personal: How committed are they to success? What are their goals? Are they written down? Do they have a plan to achieve them? Are they a self starter? Do they think everyone is? Can they work independently? Do they look for challenges?

Coaching: What is their method, approach, and style for coaching? How often will they debrief managers? What are their strategies for handling large vulnerable accounts? How will they get their sales force to ask the enough of the right questions? How much of what their sales teams tell them do they believe? What are their mindsets about money? Are they comfortable discussing it? How do they expect their team to sell? How much do they think the team should watch them? Are they more likely to ask questions, or tell the team what to do?

Motivating: How do they run sales meetings and design compensation plans? What expectations do they set and how do they communicate them? How will they continuously raise the bar? How do they recognize their managers?

Accountability: How do they handle resistance and attitude problems? Will they confront when necessary? Do they rely on lagging or leading metrics to manage performance? How patient are they when things get tough? Do they take responsibility for lack or results or find reasons elsewhere? Will they cave into discounting tactics?

Recruiting: How do they determine the right people are in the right seats? What does the ideal sales person profile and manager look like? How does that align to the ideal buyer? Do they work with or against HR in recruiting? How much is recruiting a part of the growth strategy?
Head of Sales in Consumer Goods, 11 - 50 employees
How do you manage up and manage down?

What blocks have prevented full adoption of the tech stack by the sales team?

As CEO (or other relevant position), how do you balance your time between managing the team, the product, and evangelizing the platform to potential investors?
Founder and Chief Revenue Operations Officer, Self-employed
In your opinion, what are the most important characteristics that differentiate the great sales leaders from the top, best-in-class ones? 
How have you been successful in downmarket times? In upmarket times?
What are the top challenges of being a sales leader? And how have you been successful?
How do you define - and measure - success? 
CSO in Education, 2 - 10 employees
@Carole has covered it all. 

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