Guided Tour

 Our new built-in Guided Tour gives new users – or even InsightSquared pros – a quick run-through of the features that control our reports. Some examples:

• Interval picker
• If…then filtering
• Scheduled Emails
• …and 10 others!

Interested? Click a link to check them out!

Revamped Employee Scorecard

One classic method for improving your employees’ performance is the weekly one-on-one meeting. In it, a mentor will review results, pipeline and other activity metrics as a starting point for coaching.

We’ve released to The Lab a new Employee Scorecard. Begin using it to set the agenda for one-on-one meetings today!

Risk Assessment

 Last month, we introduced risk assessment to the product in one screen. Now we’ve extended the concept throughout the product.

Use the risk assessment to determine which opportunities require action on a daily basis. Look for it in reports like Pipeline Today and your nightly and weekly emails.

Contact support to customize both how the risk is calculated and to ensure this risk assessment appears in your nightly and weekly emails!

New Report: Days Sales Outstanding

 CFOs use “Days Sales Outstanding” as a summary metric of how long it takes to collect revenue. IF your DSO is close to your payment terms, e.g. your terms are net-30 and your DSO is 35, then you are in good shape! If your terms are net-30 and your DSO is 60 then you’ve got work to do.

Best of all, InsightSquared does what QuickBooks cannot: it measures your DSO progress over time using virtual “snapshots,” so that you can track if your DSO is improving.

Contact our Account Management team to enable the DSO report for your QuickBooks data.

Contacts by Employee

The Contacts report was recently introduced to help you measure growth in your contact database and how it correlates to later events.

By popular demand, you now have a By Employee tab for the report. Check it out!

“Information is transparent and usable at much higher frequency”

A common excuse among late-adopting organizationsis that the process of collecting and analyzing large sets of information is difficult, cumbersome and time-consuming. Traditional sales reports builders on the market – including Salesforce reports – lack the intuitiveness for easy and in-depth usage. If sales managers or reps have to spend hours training and studying just to make the data usable, there will be a natural resistance to and incomplete understanding of sales analytics, making that information less effective.

Fortunately, advances in sales performance metrics, sales analytics and sales reporting software have made analytics information and large data sets more transparent and user-friendly. With the right tools, sales managers should implement data analysis with increasing frequency, eventually reaching a point of day-to-day usage.

“More accurate and detailed performance information”

Sales coaching works best on a data-driven level – when sales managers can bring precise coaching points backed up by sales performance metrics to training sessions, reps will be more receptive to improving their performances. If a rep is not reaching his or her activity goals, the data will bear that out. Performance data can also be used to compare activities among team members, creating healthy competition and providing motivation.

Another key coaching area that relies heavily on sales analytics is in pinpointing the weaknesses in a rep’s sales cycle. Studying the conversion rates between stages of a rep’s sales funnel will highlight weaknesses in their sales processes. If a rep is losing a big percentage of opportunities between demo and trial phases, they might need additional coaching to improve their qualifying or demo skills.

“Ever-narrower segmentation, more precisely tailored services”

The further a sales manager is able to drill down into target customers and market segments, the more effectively they will be able to deliver the products and services demanded. All buyer segments behave differently – comparing large and small companies, for instance – and thus, should be segmented and treated differently by your sellers.

Generally, larger deal sizes tend to have smaller win rates and longer sales cycles. Use this information to guide not only how your reps tackle these opportunities, but also in determining your expectations of how many of these deals will close and how long they will take to close.

“Sophisticated analytics substantially improves decision-making”

Data-driven sales managers rely on a wealth of information to power their key business decisions – they won’t sign off on something unless the numbers support their choices. One key area that can greatly improve with the use of more sophisticated sales analytics is in producing accurate sales forecasts. Having an outlook into the near term predictable future of the business, sales managers can determine if quotas will be met, whether more reps need to be hired to appropriately grow the team and what types of budgets or goals to be set for the next quarter or year. Looking at how the historical pipeline value is changing allows sales managers to identify early warning signals and glaring risks.

It is clear that big data has become a key point of competition and growth among sales organizations. Early adopters have gained a leg-up on their competitors, using information leveraged from sophisticated analysis to innovate and become more efficient in their processes. It is critical for late-arriving managers and companies to recognize how big data can create substantial sales value and embrace the power of advanced sales analytics.

Share your thoughts below on how your organization gains tremendous sales value from using data.

Coaching – as opposed to the directing favored in traditional sales management - works by bringing out the best in sales reps and motivating them to realize their full potential. Sales coaching emphasizes an optimistically constructive worldview, solutions instead of problems, the accountability of ownership and a holistic approach that focuses on the whole person instead of just their behaviors or performances. The best sales managers serve as guides and mentors, but not hand-holders. This distinction is crucial as managers realize the benefits of switching gears from direction-style conversations to more natural, coaching-focused discussions.

This is why the questions that a sales manager asks a rep during a coaching session are critical in setting the right mentoring and motivational tone. Deciphering the best questions to ask also benefits the coach – by using the right questions over and over again, conversations and coaching sessions will become more natural, be better-received by reps and be more valuable to the company overall. Here are 8 coaching questions that every sales manager should ask in any context.

What are you trying to achieve here / what would it mean to if you could achieve this?

Motivated people work best when they have goals to strive toward. Asking this question at the onset of any session frames the motivation for the individual rep. Additionally, asking what such an achievement would mean to them helps reps visualize the reward or end-result, which can be a powerful motivating tool.

What are your short-term and daily activity goals?

Long-term visions are just unrealistic and unattainable fantasies unless there are demonstrated short-term steps undertaken to reach that final goal. Convey to your reps the importance of setting short-term daily goals by espousing the rewarding nature of being able to regularly check important items off your list. Most importantly, give reps a way in which to track their daily activities and short-term goals so that they always feel this sense of accomplishment – or know where they need to pick up the slack.  

What exactly is going on in this situation?

Try and coax as many specific details out of the rep as possible. It will be easier for both parties to discuss meaningful progress if they can figure out exactly where they’re starting from in the first place. Additionally, getting reps to break out of their shell will foster a more collaborative working relationship, which is ultimately a great byproduct of coaching.

Why do you think this is happening?

Why questions can come off as initially accusatory – putting you in the position of a manger demanding an answer – but they make good follow-ups. Asking a rep why something is happening empowers them to diagnose the problem on their own, which is a great step toward solving their own issues.

What could you change about yourself that would bring out the best?

Throughout the coaching session, try to help the sales rep remain focused on the things that are within his or her control, namely their own attitudes and behavior. Framing the question in this manner establishes a sense of taking responsibility and accountability.

What stands in the way of achieving your goals?

Obstacles can’t be hurdled unless they are first identified. Clearly establishing the problems on the road ahead – while reiterating that this journey will not be seamless and easy – will gird the rep for what he or she will face in trying to accomplish their goals. Obstacles can also seem less daunting when they are explained and talked through, in the same way a monster under a child’s bed seems silly when you talk rationally about it.

What do you think is the best option for solving this?

Again, this empowers reps to take ownership of their own self-improvement. Their first instinct and natural inclination might be to look to you, the sales manager, for help in solving all of their problems. However, asking this question shows that you have the confidence in their abilities to solve their own issues, with the right coaxing and mentorship.

When should we meet to look at your progress?

Once you have put reps on the right path toward improving their own performances, let them know that you haven’t left them completely to their own devices. It is essential to convey to reps that you are always there to help them stay on track toward achieving their self-improvement performance goals.

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 How would you define sales coaching?

Sales coaching is someone’s complete understanding of how the entire sales process, all the people and metrics, come together. Sales coaches have to know what they are looking for in terms of process and metrics, and then be able to identify how to get the skills and techniques necessary from each individual at the highest maximum level. The sales coach is the “how-to” guy. Managers are “what-to” guys, who know what needs to be done – the coach knows how to do it. Coaches or trainers need to know what they don’t know. The best managers know the differences between managing, coaching, teaching, training, mentoring and counseling.

How does sales coaching differ from sales management?

A sales coach doesn’t have to be best manager, but the manager has to know when they need coaching. I have a guy I call my “what-to” guy, he’s the best manager in the world and knows how to communicate things, but he’s not very good at communicating how to do things. There’s a big divide between “how-to” and “what-to” – the coach is the greatest micromanager, and the manager is your macro guy.

The coach has to be able to use micromanagement as a positive – it usually has a negative connotation. Micromanagement is the best thing that you can possibly do for engagement and motivation. We call micromanagement “position coaching.” Management, by definition, is macro down to the “who should do what” level. Coaches, as noted, aren’t managing – they engage, encourage and motivate by working on the little things that make up the entire process. People need it. A lot of managers will say, “I’m not a babysitter.” Why do they say that? Babysitting is actually noble. You’re leaving your kid with a stranger! Why is babysitting bad? Your job as a babysitter is to engage and motivate the kid to go to sleep so you can watch TV. Your job as a coach is to engage and motivate reps to make money so YOU can go to sleep!

Should sales managers be sales coaches?

I think people mix it up a bit. A job as a senior executive is to find out who’s good at managing and who’s good at coaching. A lot of people are good teachers but not good coaches. [Both roles] have different routines. You don’t have to be great at everything.

I sometimes coach more than I manage. I set aside 10 hours a week and meet with 2 individuals every day for an hour each. I give every person that is a manager appointed to me 4+ hours individually with me directly a month dedicated solely to coaching.

What are some important traits of an effective sales coach?

The ability to be engaging and to motivate people. You have to know when you can get really mad at someone – will it send them off in the right way or will they break down and cry? I was a football coach and just like in sales, I had to know who I could grab in the facemask and yell in their face. Some people can’t handle this. You have to know. Your best trait has to be the ability to engage with and motivate each individual. You have to know why they are there, what they are all about. You have to be trusted. You don’t necessarily have to be liked, but your reps have to trust you. Everything you have to do in a sale you have to do as a sales coach.

Another common trait among the best coaches, leaders and managers – and sales reps! – is that people trust them. Give me the 51% of people who want to get better and will follow me because they believe in what we were doing together and that I will win every single battle.

Do you believe in data-driven sales coaching? How have you used analytics and data to supplement your sales coaching?

Yes, yes, yes, yes, yes! It’s ALL about the data. Data drives all your decision-making. Every metric matters. Some of them are wrong, by the way. The key is to figure out what’s working and what’s not. You have to have enough data to figure out what’s working. You don’t coach artists. We’re not artists – we have a job, a process.

Our sales process goes from the meet or qualifying stage to engagement, the building of rapport to the building of trust. How long are they at each stage? What qualifying questions should have been asked? How do you price the transaction based on the questions you’ve asked? How many of these leads in that stage turn into deals and how long does that take? I know the aggregate numbers so if your individual metrics are off, why is that? I know how many offers you need to make, how many calls you need to make, how many leads you need, how many deals are in the final stage of the pipeline. I know the volume targets, the dollar value targets. All that stuff drives how people are doing or what they need. For instance, I had a coaching session today. This rep had a high number of transactions, but not the dollar value of other reps. Why? She was pricing her deals incorrectly, so the metrics tells us that we have to work on that.

How do your sales coaching sessions with individual reps generally work? What is the process like?

My coaching meetings are very individualized and customized. Reps have to bring me their performance goals, and then we create the necessary actions from there and measure them. Coaching sessions work better when they come up with their own goals, because then they’ve already bought into them and you don’t have to micromanage the crap out of them. I have all the important metrics in mind – the key is to get the reps focused on and talking to us about those metrics.

How has your background in athletics administration and coaching impacted your sales coaching process?

Some of the best coaches I ever worked with figured out how to get to the bottom of issues. They figure out how to prepare better than anyone else – preparation is the key to everything. After that, you learn by making mistakes. You have to be able to say that you were wrong.

Athletics is different in that there’s a defined season or time frame that will end. You have a much longer time frame in sales and with that people you work with. You have a longer window to get people to be better and better.

Other than that difference, it’s exactly the same parallel (between sales and athletics coaching). Baseball actually has it set up the best – you have a manager overseeing everything. The hitting coach focuses only on teaching hitting; the pitching coach focuses only on instructing pitchers. You have coaches who focus on specific in-game situations, like the third base coach. Football is similar, where the head coach is the manager, making sure everyone is doing the right thing, without X’s and O’s. The bench coaches and the position coaches, they actually teach and coach skills. Baseball really has [the differences between coaches and managers] down perfect.

Where do you see inside sales trending in 2013?

I have a strong opinion on this – I don’t see a great difference between inside and outside sales. For example, many of my inside sales people actually have to travel. We start from the inside-out but we get on airplanes all the time. It’s not a hybrid – we’re inside sales – but we will get on the airplane to do certain things. If the trust isn’t there yet, we have to build better trust before we finalize transactions. But we still close deals worth millions of dollars on the phone all the time. I see inside sales as the only way to go. The same way that football coaches can call timeouts, we can do that with our inside sales teams as well. Call timeout whenever you want, take the reps off the floor for a breather and some coaching.

A trait to develop to be successful at managing inside sales – you have to understand that everyone’s different. We all try to put square pegs in round holes. You have to figure out what people can do well. I get in the way more often than not when I put people in a position that I want them in, instead of the position they should be. There’s no such thing as a perfect person. That’s real life. I don’t have to work as hard at some of the things I do, some things come naturally to me while others are a struggle. Inside sales reps are the same.

What are some of the biggest and most common challenges in sales coaching today?

The biggest challenge is in not dedicating enough time for management to do it. We took people off the sales floor three times a week for 35 minutes each time. I had five different groups every day for seven months in a row and their sales went up. I took them off the floor whenever I could. The hardest thing is simply finding the time.

The second hardest thing is to coach people who are your peers. Then, it becomes more like mentoring. Mentoring is “watch what I do.” A coach is more like “let’s try it this way.” A coach has to be willing to lose. They don’t take the credit, they give credit. Coaches lose games, players win them. Anyone who thinks differently doesn’t have it right. You have to be willing to take the hit every time you lose. A bad coach in business is one who says, “I told that person to do that a thousand times!” That coach has failed. The hardest thing to do is to blame things on yourself. It’s not always about my way; it’s not necessarily the best way.

Find out more about Gary and Stone Street Capital, LLC at http://www.stonestreet.com/ or follow Gary on LinkedIn. 

Timing

Time kills all deals. Look at the opportunity age vs. your average sales cycle (i.e. win cycle). Also if the opportunity is sitting in first two stages longer your historical won cycles for those stages, then they are “stuck opportunities” and should be flagged as at risk.

Average Deal Size ($)

Review the expected opportunity size vs. your average won deal size. If your opportunity is 3x greater than your average, it should be treated differently than your regular opportunities. Larger deals have lower close rates and longer sales cycles than smaller deals, so if the sales rep is not treating the particular opportunity differently then it’s at risk. Also note if the expected deal size of a given opportunity dropped by more than 30% in later stages then it may be at risk.

Slippage

Opportunities that are pushed often or slip beyond the expected close date should be flagged as at risk. If a deal’s close date has pushed more than 3x then it should be flagged as at risk.

Stalled Engagement

Opportunities that are forecasted to close soon should be actively engaged with by reps. If an opportunity displays little to no rep activity over the past two weeks, it has likely stalled, diminishing the chances that this deal will close so it should be flagged as at risk.

Stage

An opportunity in the first stage of the sales cycle does not belong in the sales forecast, even if the rep marked the expected close date in the current selling period. Additionally, make sure that for every opportunity (at any stage), your reps know clear next steps that the contact will take. Otherwise, the opportunity must be flagged as at risk.

 Negative Velocity

If there is negative velocity (or deal is stalling for a longer period of time in the last few stages) then it should also be flagged as a deal at risk.

Title

By the time the opportunity reaches the late stages, your reps should be talking to a contact who has a title of your typical buyers. If your champion still has to ask for permission at this late stage from others with authority at his company then the opportunity is at risk. If the rep is not already talking to these other executive sponsors at this late stage then this opportunity must be flagged as at risk.

Lead Source

Figure out what your win rates are for each lead source. If an opportunity comes from your low-probability source, it should be flagged as at risk.

No competitor

Typically, customers will shop around to compare products and prices. If during late stages in the buying process, your sales rep is not aware of which competitors his contact has looked at, then that opportunity should be flagged at risk.

Late Random Additions

Look closely at any large deals (that are more than 2x the average deal size) that were randomly added at the last minute. These should be flagged as at risk.

Keeping track of these 10 sales forecasts killers will allow sales managers to make more accurate sales forecasts.

What other sales forecasts killers would you add to this list?

As discussed in a recent blog post, the best managers – and especially sales managers – are, first and foremost, masters at coaching. They provide guidance and encouragement to help employees facilitate the discovery of the right path while achieving stellar results. However, there is some confusion about the definition of sales coaching, especially due to some definitions of coaching in sports, which may not perfectly translate to coaching as a sales manager.  So, let me first define coaching, and then define sales coaching.

What is Coaching?

According to the International Coach Federation, coaching is defined as, “An interactive process to help individuals and organizations develop more rapidly and produce more satisfying results; improving other’s ability to set goals, take action, make better decisions and make full use of their natural strengths.”

In Masterful Coaching, Robert Hargrove describes coaching as “challenging and supporting people in achieving higher levels of performance while allowing them to bring out the best in themselves and those around them.”

A coach is one who combines elements of a teacher, a counselor, a guide, a cheerleader, and a facilitator who uses the Socratic Method. A coach should understand the person’s motivations, assess their strengths and weaknesses, encourage and inspire them to achieve greater results, adopt a unique approach with each individual (instead of a one-size-fits-all approach) and foster an environment that allows the individual to thrive and become successful.

Coaching is different from managing, training, or mentoring. Traditional, old-school managers generally focus on telling people what to do. They don’t typically micromanage or drill down to the nitty-gritty of how individuals should do things.

Telling people what to do is not coaching. People don’t like to be told what to do, but rather, prefer to be enabled and helped. They want to be involved. As the old maxim goes, “Tell me and I forget, show me and I remember but involve me and I learn.” Coaching subscribes to this adage, involving employees to improve their job performances. It emphasizes the development of individuals and improving their performances gradually, which is a more practical approach than telling people what to do, which will be met with resistance.

The future of management is coaching. Old-school management methods are not effective anymore. One example of that is that it has been well-documented that the new Gen Y employees have different values and traits and because of that Gen Y does not work effectively within the scope of traditional management.

Coaching focuses on people’s strengths, not their weaknesses. Sports coaches constantly train to improve their players and focus on making them better every day. Coaches in sports seek to emphasize their best players’ strengths, more than they focus on improving weaknesses.  When a football coach works on a quarterback’s strengths, he might focus on improving his accuracy or decision-making to help him improve as a quarterback. It would be silly for him to improve at being a wide receiver and work on his catching or route-running.

Nathan Jamail had a great point in his book The Sales Leader Playbook. To paraphrase him, “The best players do not necessarily win because they always execute the most difficult plays. They simply practice the basics, what’s tried and true, and get winning results. Focus on strengths and practice the basics until your players and sales teams are great at these basics.” This is what good coaches do with their teams – they focus on strengths and help their teams practice the basics.

What is Sales Coaching?

Although they might be a Sales Manager in title, they have to be a Sales Coach in function. Sales coaching, like any other type of coaching, requires a unique approach to each sales rep and not a “one size fits all” approach. A sales coach will not be able to manage the results but he or she can manage the behaviors or the steps that the sales reps take to get to those results.

Chris Lytle said in his book The Accidental Sales Manager, “You’re the sales manager but you don’t manage sales. You must coach the players to do what it takes to win instead of trying to coach the score.”

Keith Rosen said in his book Coaching Salespeople into Sales Champions, “Management is dead. Sales managers can’t just become sales coaching by changing their title without changing their skill set. The coaching model is based on the belief that the question is also the answer and that the coach is responsible for finding the answers themselves and developing their own problem-solving skills. Coaching uses a process of inquiry so that people can access their own energy or inner strength to reach their own level of awareness. Tapping into a person’s previously unused strengths and talents advances personal growth and learning, which challenges people to discover their personal best. Coaching is collaborative as well as interactive.”

Noted sales coach Gary Milwit said in an interview, “Some of the best coaches I ever worked with figured out how to get to the bottom of issues. You learn by making mistakes. You have to be able to say that you were wrong.”

An important thing to note is that to be an effective sales coach requires knowing each individual rep’s key performance metrics. Sales is a science, and sales managers must manage their team by analyzing metrics and KPIs or they will quickly lose the respect of their reps. Just like any coach, a sales coach draws from his or her experience, but the truly successful sales coaches or sales managers are data-driven and analytical. They ensure the successful performances of their reps by measuring hard data and subsequently measuring improvement and progress after coaching sessions.

Sales coaching is the new sales management. It helps promote individual rep’s development, improves job performance and reduces unnecessary learning time. Another key benefit is that sales coaching helps retain top performers. Unlike sales management, which focuses on telling them what to do, coaching helps reps who are already high performers become even more effective and successful.

Are you a good sales coach? What approaches do you use to coach your reps?

Keynote speaker General Stan McChrystal, the former commander of U.S. and international forces in Afghanistan, delivered a great speech.  General McChrystal inspired the audience by regaling them with anecdotes from his military career, drawing parallels for effective sales and management leadership.

Our own CEO Fred Shilmover was on hand to give a presentation on “Implementing the SiriusDecisions Demand Waterfall Framework for Inside Sales Driven Sales and Marketing Teams.” Fred’s presentation focused on the importance of having Definitions, Processes and Systems in place for proper flow and attribution from top of the funnel marketing to conversions, sales and revenue. The case study focused on InsightSquared’s use of Salesforce.com, Shoretel Sky and InsightSquared’s own Sales and Marketing Analytics Product to successfully implement the Demand Waterfall.

InsightSquared depends on a combination of Inbound Marketing and Outbound (Teleprospecting) Demand Generation. Creating discrete flows and measurement is challenging, but critical in order to measure effectiveness and ROI on a particular channel.

To accomplish this, sales and marketing teams must have agreed-upon definitions of and consistent metrics for tracking and measuring  each inventory state, as well as each transition – for example, from Marketing Qualified Leads (MQLs) to Teleprospecting Accepted Leads (TALs). Each team that can more effectively align their processes and implement the framework with the right systems. This alignment of marketing and sales processes, while tracking which inbound and outbound sources demand and leads are coming from, is delineated in the SiriusDecisions Demand Waterfall, pictured below.

Yet, many organizations continue to struggle implementing the SiriusDecisions Demand Waterfall with their Salesforce.com CRM. Without proper implementation of the Demand Waterfall and alignment between marketing and sales, attribution and accurate measurement of ROI becomes a nightmare.

For too long, marketing and sales have been treated as disparate parties, instead of equal partners. As the theme of the Summit – and Fred’s presentation – emphasized, sales and marketing should not only collaborate on goals, definitions and processes, but also share each other’s anxieties and successes.

Does your organization struggle to implement the SiriusDecisions Demand Waterfall with your Salesforce.com CRM? Are you having trouble aligning your marketing and sales teams? Email us or drop a comment below to learn more.