The Surprising Road(s) to Demo and Presales Mastery


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This article explores the road(s) towards demo and presales mastery – and may change your perceptions whether you are experienced or new to the discipline. 


Ask yourself, honestly:  where am I in my journey to demonstration and presales mastery? 


If you answered, “I have truly mastered both of these, without question!” then you are welcome to skip this article (but you are at great risk…!).


If you answered, “Well, I think I may have achieved mastery…” then definitely read on.


If you answered, “I’ve made good progress, but there’s certainly further to go…” then you are likely well along your journey – what options are available to you along the way?


And if you answered, “I’ve just started…” then this article should provide you with some surprising and helpful insights.


Let’s explore the journey!


The Curse of Knowledge


“It is what we know already that often prevents us from learning.”

– Claude Bernard


The biggest obstacle to ongoing learning is getting good at something.  Why?  Because we develop habits and grow complacent – and habits preclude change.


Anyone who claims that they are “at the top of their game” is at risk of this complacency. 


In presales, we are challenged to stay on top of our constantly evolving products, changing technologies, new products and new markets.  This often consumes a large portion of our time.  Customer deliverables (such as doing research, Discovery, demos, POC’s, etc.) demand the majority of our day – with internal meetings, administrative tasks, and the daily detritus competing for the remaining hours. 


We develop habits to cope with this mayhem.  And while habits are extremely helpful, they resist change – and they similarly resist ongoing learning. 

The North Face has a terrific motto, “Never Stop Exploring” – which we can gently modify to “Never Stop Learning” and apply it to our quest for demo and presales mastery.


Do You Know What You Don’t Know?


“It’s what you learn after you know it all that really counts.”

John Wooden, UCLA Basketball Coach


Malcolm Gladwell commented in his terrific book “Outliers” that in many disciplines it can take 10,000 hours of practice or experience to become a “master”.  Note that this applies differently to diverse arenas, but it is still a good rubric. 


Up through present times, “apprentices” learned a trade and became “journeymen”.  After a lengthy period of time (perhaps 10,000 hours), individual journeymen became recognized as true “masters” of their professions.  These masters not only can execute their trades in a consistent, highly competent manner, they also often expand their practices, testing and incorporating new ideas and methods.


These same ideas apply to the worlds of demos and presales – and demo and presales “mastery”.  A few comments, accordingly:


1.     Anyone who announces that he or she is a “master”, likely is not…!  This is, frankly, braggadocio and represents a precarious stance.  If others say that someone is a master of presales, then he or she has firmer footing.


2.     Regarding 10,000 hours, in a typical trade that is 100% focused on the practice, accumulating 10,000 hours would take about 5 years (based on 250 8-hour working days per year – and assuming no other activities other than the specific trade practices are counted). 


In the world of demos, if we assume that a presales person invests 2 hours per day on demos (including preparation, delivery and follow-up, training, and all other demo-related activities), then reaching 10,000 hours takes about 20 years.  4 hours of dedicated demo activity per workday yields 10 years.


And that’s just for demos – only one portion of presales practices.  Does this seem reasonable?  Absolutely!  Consider:


From Consensus’ terrific “2020 Report:  Sales Engineer Compensation and Workload”, it was found that it may take 2 years “to mint a fully fluent sales engineer”. 


That’s the time it may take to move from apprentice to journeyman.  That’s likely covering the basics – sufficient product and technology knowledge, company background, basic competitor understanding and positioning, simple Discovery skills, basic demo skills, whiteboarding, executing POC’s, conference and trade-show participation, and perhaps participating in an RFP response or two.


However, there is a great deal more to achieving presales journeyman status (and mastery is still over the horizon, frankly).  One needs experience across a broad range of other presales activities to become a competent journeyman…


Time to hit the road…!

The Journey Begins – Let’s Start with Demos


“In theory, there is no difference between theory and practice. But in practice, there is.”

– Yogi Berra


Most would agree that preparing and delivering demos is a key task (and pleasure!) for presales practitioners.  Once a new presales person has achieved competency with basic product demos and completed onboarding (and hence his/her apprenticeship), the road to journeyman status begins.


This path needs to cover a lot of territory, including:


A range of demo types and situations:

        Introductory demos

        Overview demos

        “Deep dive” demos

        5 minute demos

        1-2 hour demos

        2-4 hour demos

        All day demos

        Multiple-day demos (ick)

        Demos for individuals

        Demos for small groups (e.g. 2-10 people)

        Demos for large groups (e.g. 11-50 people)

        Demos for huge groups (100’s of people)

        Demos at conferences

        Webinar demos

        Trade-show demos (for those still doing tradeshows and booth duty)

        User-group demos

        Upsell and expand demos

        Renewal demos (and dealing with down-sell situations)

        New release demos

        New product demos

        Market development demos

        Executive Briefing Center demos

        Demos in support of channel partners and resellers

        Demos to other 3rd parties and analysts

        Marketing demos and recorded demos

        Internal demos (to developers, customer success, and other departments)

        (For Great Demo! graduates, most of these translate to various dialects of Vision Generation and Technical Proof demos, but with numerous changes and modifications)

And variations of the above:

        Single-product vs. product-suite offerings vs. multiple product lines

        Accommodating regional and cultural differences

        Embracing the interests of executives vs. middle managers vs. staffers vs. administrators – individually and when two or more are combined in a single session.

        Mapping to Early-Adopters vs. Early Majority vs. Late Majority vs. Laggard customers

        Highly transactional sales vs. mid-market vs. enterprise spaces

        Individual buyers vs. committees; multi-regional and multi-national committees

        Communicating value

        Operating effectively over the web (beyond saying, “Can you see my screen…?” followed by click and talk, click and talk)

        Making the complicated look simple

        Introducing competitive differentiators (sometimes referred to as “setting land mines”)

        Surviving Scripted demos (delivering RFP-response demos and associated processes)

        Applying analogies and metaphors


        Applying props and visual aids

        Involving multiple platforms (e.g. Macintosh and Windows, mobile phones, tablets)

        Involving customer players (e.g. your champion)

        Use of Informal Success Stories and other references

        Applying demo “self-rescue” techniques

        Managing questions

        Managing bugs and other anomalies

        Dealing with hostiles

        Dealing with “smartest-person-in-the-room” situations

        Managing “burn victims”

        Demo meeting management (time, set-up, human and other resources, etc.)

        Demo follow-up – closing the loop with your CRM system, sales team members, other internal organizations, and your customers

        Securing the order with the least expensive form of proof (e.g., reference vs. demo vs. POC)

        Providing feedback to your team on demo “wins” and “loses” – feedback on success presenting key features, screens (Illustrations), use cases, tips and techniques

        Providing feedback and improvements to your demo environment

        Bug reporting

        New feature requests, use cases and rationale

        Feature implementation feedback to product management/development

Sales team demo aspects:

        How demos fit (or don’t fit) within your organization’s sales methodology and processes

        Working (productively) with one salesperson

        Working with a team of two or more salespeople

        Working with the best salespeople

        Working (productively) with the worst salespeople

        Working with SDR’s and BDR’s

        Working with Inside Sales folks

        Managing (and resolving) disagreements within the sales team

        Bringing a new salesperson up-to-speed with your demo process(es) and methods

        Working with channel partners and resellers

        Demos with multiple presales presenters (in a single customer meeting)

        Demos with multiple presales and other department presenters (e.g., Product Management or Professional Services in a single customer meeting)

        Picking up or transferring sales projects to/from you


[This list is not exhaustive – but is certainly exhausting…!]


That’s a lot of time on the road (or virtual road) – quite the journey so far.  Let’s pause for a rest and pull out the (virtual) map to see where we’ve been…


Assessment Time!


As you review your expedition so far, what have you seen and experienced?  What are the skills and know-how that you have collected?  Let’s assess your trip so far…! 


If you can honestly check off (or tick off) each of the items above (those that are relevant to your role), then you are likely a journeyman, with respect to demos.  Congratulations!


[Sadly, many presales folks who consider themselves “skilled at demos” have developed and present a rather fixed demo pathway and pride themselves on being engaging – but only adjust their pathways slightly to accommodate the enormous range of requirements and situations.  People at this level have not yet become journeymen (but often don’t realize it!).  They don’t know what they don’t know.]


You can use the list above to assess your status and progress towards full journeyman status.


First, identify those areas that are relevant to your organization and role (and add any that are missing).  Then assess yourself – consider using a scale to rate yourself (how about 1-10?) with respect to competency in each area.  Where are you strong?  What areas could see improvement?


And what areas were you unaware of?  (Do you now know what you didn’t know before?)


Next, ask a trusted peer to do the same for you – and then your manager.  How do all three assessments compare? 


Discuss any significant gaps between your assessment and others – this is key!  Then select areas of focus and set small goals to improve. 


Achieving Presales Journeyman Status – Broadening Your Horizons


So far, we’ve largely been discussing demos – just one (crucial) aspect of the presales role.  What about:


        Qualification – Inbound vs. outbound leads

        Qualification – Marketing Qualified Lead vs. Sales Qualified Lead vs. Demo Qualified Lead vs. POC Qualified Lead

        Basic Discovery skills – evaluating technical “fit”

        Deeper Discovery skills (this alone can take years to develop) – workflow analysis, cultural and other Discovery aspects (e.g., “beyond the workflow”)

        Incorporating Customer Success profiles into qualification and Discovery processes and conversations (focusing on those prospects most likely to succeed)

        Cultivating and working with technical and business champions and coaches

        Buyer enablement (another broad, yet largely unexplored topic)

        Setting-up and managing POC’s, Sandboxes, Trials and Workshops (beyond simple execution)

        RFP response strategy and execution; RFP seeding

        Advanced presentation skills (both face-to-face and over the web)

        Advanced web communication practices (remote demos, presentations, discovery, whiteboarding, workshops, etc.)

        Value analysis and ROI analysis

        Technical proposal drafting

        Technical sales content development

        Becoming a subject matter expert in one or more products or arenas

        Presales tools exploration and use (internally developed and commercial)

        Trade-show practices

        Conference and trade-show presentations and workshops (beyond booth duty)

        Webinar content generation and delivery

        Relationship management

        Technical account management (yes, there is a counterpart to sales account management)

        Trusted Advisor skills (yes, there are specific, trackable skills and steps to achieve Trusted Advisor status)

        Post-sales support and related activities

        Hand-offs to customer success teams

        Project management (when appropriate)

        Harvesting references

        Saying “no” or “not yet” gently, yet firmly

        Mentoring and coaching skills (with peers)

        Time management

        Identifying and scheduling personal growth and development opportunities

        Negotiating and tracking on personal goals and metrics



Open up your map and let’s assess again – how are you doing with respect to these waypoints?  (Note – this is definitely a starter list…)


We Head Uphill…


We hope your journey so far has been pleasant – winding along gentle, smooth highways, past pretty valleys and steams…  Because now we’ll shift gears for some mountain roads with steep grades – welcome to presales management!


The road to presales mastery includes the key skills of hiring, firing, assessing, and developing your team (in addition to yourself).  Here your journey will likely include:


Presales (frontline) management skills

        Determining your role – manager-player-coach or pure manager-coach

        Assessing your team, setting and tracking goals

        Performing and tracking periodic reviews

        Developing your team

        Learning how to coach, as a manager

        Coaching, as a manager

        Creating and managing a budget

        Purchasing and deploying tools

        Recruiting, interviewing and hiring new team members

        Onboarding new team members (both from internal and external sources)

        Dealing with HR issues within your team

        Firing employees and load redistribution; RIF’s and furloughs

        Region and quota changes

        Compensation plans (managing existing)

        Implementing new compensation plans

        Changes to the sales organization and realignment of your team

        Relationships with other teams and internal organizations

        “Letting go”

        Continuing personal growth and development

        Time management



The road has gotten more difficult – but the views are often more rewarding. 


Your journey continues as you gain experience and explore new paths – and now you’ve just been promoted to a senior presales management role – congratulations!  What new challenges do you face?


Presales (senior) management skills

o   Most of the above, plus

o   Defining presales strategy, drafting and communicating associated plans

o   Establishing and communicating policies

o   Developing your managers

o   Teaching your managers to coach

o   Creating, distributing, and managing a budget

o   Purchasing and deploying tools

o   Recruiting, interviewing and hiring new front-line managers

o   Developing onboarding plans

o   Defining and/or re-organizing global/country/large region organizational structures and quotas (e.g., for North America, Latin American, EMEA, Asia Pacific)

o   Redefining strategy with respect to a major new competitor or disruptive technology

o   Defining organizational metrics

o   Establishing and guiding an enablement team

o   Establishing and guiding a presales operations team

o   Creating and rolling-out compensation plans

o   Negotiating for resources

o   Organizing and managing global internal roll-outs and conferences

o   Opening new field offices

o   Establishing strategic 3rd party relationships

o   Developing customer “360-degree” programs

o   Continuing personal growth and development

o   Organizational time management

o   Establishing a C-level seat for presales

o   Becoming an industry spokes-person or thought-leader

o   Etc.


You are in the mountains – and the views from the peaks across the broad landscape are terrific. The air is fresh and clear at these elevations (but breathing takes more work).  Where else could the road lead?


Perspective – The View from Abroad


“It’s what you learn after you know it all that counts.”

– Harry S Truman


Where indeed…  What if you could see those same peaks from another mountain range? 


Achieving presales mastery includes gaining a 360-degree view of the role, often by moving to (or coming from) roles served and engaged by presales, such as:


        Sales (gasp, yes, sales…!)

        Professional Services and Implementation

        Other Consulting roles

        Customer Service and Support

        Customer Success


        Sales or Presales Operations

        Product Management

        Product Marketing

        Partner and Channel Marketing or Support




If you’ve done nothing but presales, you may be very strong in your role, but you lack the additional perspective gained investing time in one or more of these other functions.  It can be truly enlightening to see presales through the lenses of other functions. 


Similarly, have you always operated in a single region or area?  Have you always worked from the same office?  Take your journey beyond the end of your local roads!


Consider heading to another area or country.  Moving overseas or to another country provides some rather eye-opening views and perspectives – particularly if you move to or from your HQ to a regional office organization!


Consider the example of moving from a U.S.-based HQ to an office in Europe:


        You’ll be working with new team members and (likely) new customers

        Multiple languages (likely)

        Different local business customs and cultures

        The subtleties of U.S. English vs. local versions

        Seeing “HQ”, um, differently

        Learning and adapting to non-work day-to-day life overseas (or over borders)

        Adapting to A4 paper…


Interestingly, many Dutch and German companies routinely sent developing managers overseas to gain insights into local culture, business practices, and the challenges of running operations and communications abroad.  This provided terrific first-hand experiences that could be applied when these same managers returned home to assume larger roles.

Note also that your “road” has morphed into a range of transportation methods – walking, climbing and hiking, various bicycling types, driving cars, trucks, and other vehicles, flying, marine travel – your journey has become a delightfully rich experience!


And Now for a Completely Different Perspective – What Does the Road Think About All of This?


By you’ve now traveled many miles and kilometers on a delightful variety of autobahns, highways, byways, dirt roads, oceans, tracks and trails, both at home and aboard – what perspective is missing?


Everything through this point has you (or the developing presales journeyman) acquiring additional skills and experiences – but they are all oriented from the perspective of the vendor, selling software to customers.  What critical element is missing from this equation?


Being a customer.


It is one thing to create and deliver thousands of demos – it is quite another to be on the receiving end of hundreds of demos from vendors, seeking to engage you and asking you for $150,000 in return for a few hours in a demo meeting…! 


Few things open your eyes like being the customer (particularly the key contact, champion, or main decision-maker), as you invite vendors to consume you and your team’s time in a series of demo meetings while you evaluate your options and move towards a decision. 


These experiences complement and offer contrast to everything you’ve experienced while operating from the vendor’s perspective:


        How do vendors interact with you – are they aggressive sellers or enable your buying process?

        Are you assaulted by SDR’s and BDR seeking to “qualify” you before turning you over to their sales team (or are they helping to establish a partnership)?

        How much Discovery do they do (if any) prior to inflicting demos on you and your team or are they skilled at helping you define your full problems and needs statements?

        How do they respond (or pro-act) regarding your questions and needs in your buying process?

        What pressure do they apply towards the end of their quarters (or do they map to your Critical Dates)?

        How do they handle winning the business?  How do they handle losing the business?  How do they respond when you choose to do nothing (“No Decision”)?

        Post-sale, how is the hand-off from their sales team to their implementation folks, to their customer success managers – are they proactive or do they panic and scramble when you remark that you might not renew the subscription (are they truly interested in your success)?

        How do they respond to your requests for new features and insights into product futures?

        Is there a Users’ Group that provides value to you?

        Are you asked to serve as a reference or present at a conference – how is this managed?


Experiencing the customer side of the journey is essential to achieving true presales mastery.  It is good if you were a customer player at one time; ever better if you were in a position of power and authority.



Mastery and Rethinking


“There is a way to do it better. Find it.”

– Thomas Edison


For thousands of years, the fastest forms of travel for humans were by horse on land and by wind on the seas.  In a span of less than 100 years, automobiles, railroads, airplanes and combustion-driven ships supplanted the traditional approaches to transportation.  The journey evolved.


In software, we’ve moved from terminal-based technologies, to client-server, to SaaS – and hardware has evolved from terminals and card-readers feeding huge computers, to mini-computers, to micro-computers (desktop machines and laptops), to tablets and incredibly smart phones.


True mastery questions the status quo


A master in any discipline is constantly asking, “Can we do this better?”  In many cases, this represents ideating, testing and implementing small changes.


But true mastery questions the status quo and asks, “What if we throw out the traditional approaches?  What if we explore new directions, new methods?  What if we apply new tools and technologies?”


The same principles apply to presales and demos.


Interestingly, the Great Demo! methodology resulted from a realization that traditional demos (the status quo) were painful to customers.  And while the results from traditional demos seemed acceptable (as did riding a horse to town), it was clear there should be a better way.  So we scrapped the traditional approach and started fresh – yielding a substantially improved method – a step-change in the world of software demos (Do the Last Thing First!).


And correspondingly, Great Demo! continues to evolve, embracing and testing new ideas, exploring new technologies and addressing new challenges.  (Explore our blog and articles for these…)


The journey towards mastery is just that:  a journey with, perhaps, a destination that can never be reached!


Are We There Yet?


“I am still learning.”

— Michelangelo


Perhaps attaining true mastery in any discipline means that once you have mastered all there is to know, you put it aside and try a new direction…


Perhaps – decide for yourself. 


In my case, have I achieved presales mastery?  Have I achieved demo mastery? 


Not yet…!



Copyright © 2020 The Second Derivative – All Rights Reserved.

Republished with author's permission from original post.

Peter Cohan
Have you ever seen a bad software demonstration? Peter Cohan is the founder and principal of Great Demo!, focused on helping software organizations improve the success rates of their demos. He authored Great Demo! - how to prepare and deliver surprisingly compelling software demonstrations. Peter has experience as an individual contributor, manager and senior management in marketing, sales, and business development. He has also been, and continues to be, a customer.


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