Ask Better Questions

“Be a good listener,” Dale Carnegie advised in his 1936 classic How to Win Friends and Influence People. “Ask questions the other person will enjoy answering.”  Effectively asking questions is a big part of a leader’s job. Good decision-making is based on information we obtain by asking the right questions. Making a sale, including handling objections, is also supported by effective questioning.

Many of us hesitate to ask questions, unfortunately. Sometimes it’s because we don’t want to be perceived as intrusive. Other times,  we worry that our questions may be viewed as silly and make us appear incompetent.  On the other hand, one might assume that more information is not necessary.  In every instance, an opportunity to obtain valuable information is lost.

Alison Woods Brooks, an Assistant Professor at the Harvard Business School who teaches Negotiation and is affiliated with the Behavioral Insights Group and Leslie K. John, Associate Professor of Business Administration at the Harvard Business School, understand that effective questioning is a skill that can be honed to make our conversations more productive.

The two offer guidance on the best type of questions to ask, tone of voice to use, the sequence of questions and how to frame the questions.  The best approach for a given situation depends on the goals of those in conversation.  Is the discussion  cooperative (e.g., relationship-building or accomplishing a task together) or  competitive (the parties seek to uncover sensitive information from each other or serve their own interests), or some combination of both? Brooks and her research team employed human coding and machine learning to identify four types of questions:

  • Introductory questions (“How are you?”)
  • Mirror questions (“I’m fine. How are you?”)
  • Full-switch questions (change the topic entirely)
  •  Follow-up questions (solicit more information)


Although each question type flows naturally in conversation, follow-up questions have special power. Follow-up questions signal to your conversation partner that you are listening, that you care and that you want to know more. People interacting with a conversation partner who asks lots of follow-up questions tend to feel respected and heard. According to Leslie K. John, “Most people don’t grasp that asking a lot of questions unlocks learning and improves interpersonal bonding.” Plus, follow-up questions don’t require much thought or preparation and usually come naturally to the questioner.

Yet be advised that no one likes to feel interrogated. Furthermore, closed-end questions tend to yield one-word answers. Open-ended questions counteract that effect and for that reason, they can be particularly useful in uncovering information or learning something new. In fact, they are wellsprings of innovation—which is often the result of finding the hidden, unexpected answer that no one has thought of before.


If the goal is to build relationships, opening with less sensitive questions and escalating slowly seems to be most effective.  In a set of studies (the results of which went viral following a write-up in the “Modern Love” column in the New York Times), psychologist Arthur Aron recruited strangers to come to the lab, paired them up and gave them a list of questions.  Participants were told to work their way through the list, starting with relatively shallow inquiries and progressing to more self-revelatory ones, such as “What is your biggest regret?”

Pairs in the control group were asked simply to interact with each other. The pairs who followed the prescribed structure liked each other more than the control pairs. This effect is so strong that it has been formalized in a task called “the relationship closeness induction,” a tool used by researchers to build a sense of connection among the participants.


People are more forthcoming when you ask questions in a casual way, rather than in a terse, official tone. In general, an overly formal tone is likely to inhibit people’s willingness to share information.

Group dynamics

Conversational dynamics can change profoundly depending on whether you’re chatting one-on-one with someone or talking in a group. Not only is the willingness to answer questions impacted by the presence of others, but members of a group tend to follow one anothers lead. In a meeting or group setting, it takes only a few closed-off people for questions to lose their probing power.  Conversely, if even one person starts to open up on a topic, the rest of the group is likely to follow suit.

Art of the response

Conversation is a dance, a mutual push-and-pull. Just as the way we ask questions can facilitate trust and the sharing of information so, too, can the way we answer them. Answering questions requires making a choice about where to fall on a continuum between privacy and transparency.  How should I answer this question? Assuming that I answer, how forthcoming can I afford to be? What should one do when asked a question that, if answered truthfully, might reveal a less-than-flattering information, or put one in a disadvantaged strategic position?

Each end of the spectrum—fully opaque and fully transparent—has benefits and pitfalls.  In negotiations, withholding sensitive information (e.g., that your alternatives are weak) can help you secure better outcomes. At the same time, transparency is an essential part of building meaningful connections. Even in a negotiation context, transparency can lead to value-creating deals; by sharing information, participants can identify elements that are relatively unimportant to one party but important to the other—the foundation of a win-win outcome.

Thanks for reading,


Photograph: The Dating Game, 1965- 1973 (ABC-TV)




The Post-Speech Q & A

Everything has gone swimmingly with your presentation. The room is full, you held the attention of audience members and your timing was spot on. There are 10 minutes left for the question and answer session. You think you’ve won, but you have no idea how vulnerable you are.

Speakers often don’t realize it, but those brief minutes in the post-speech Q & A session have the potential to become your Achilles’ heel. The post-speech Q & A is un-mapped territory. You don’t know what’ll be thrown at you. The Q & A is a variable that few speakers prepare for, because they assume they can’t prepare for it and so they wing it and figure they’ll muddle through. Not!

As Tesla CEO Elon Musk now knows, winging the Q & A can be a grave mistake. At the conclusion of a May 2018 investor’s meeting speech, Musk had a heated exchange with a financial analyst who asked a couple of apparently incisive questions. Musk didn’t come out of it looking good. You may have heard that Musk has recently said “lack of sleep” and “stress” have been wearing him down. Sorry, it’s a weak excuse.

Executive Coach and speaker John Millen points out that when speakers mishandle post-speech or other questions, they can appear uninformed, hostile, or even dishonest. “How leaders answer questions is enormously important in building trust. If you come into a high-stakes situation talking to investors, employees, regulators (or a potential client) and you don’t communicate properly, there can be huge problems.” So let’s consider tactics that can bring you through your next post-speech Q & A with flying colors.


Take all precautions to avoid being perceived as clueless, shady, or defensive. If a question is posed for which you don’t have an answer, say “That issue is under review and I don’t yet have enough information to answer.” You can also turn it around and ask the questioner “Why is that important to you?” The answer may open your eyes to aspects of the subject that you had not previously considered and can be a teachable moment for you.

Start the process by thinking your subject through so that you can anticipate questions that could be asked. Next, do some audience research and ask the program organizer if there might be audience members who could oppose your goals or point of view, so you can rehearse answers designed to neutralize a campaign to undermine you.


Be mindful of aspects of your speech that could potentially seem controversial to certain audience members. A good defensive tactic is to proactively address a possibly sensitive matter in your speech, preferably toward the end or in your concluding remarks. Acknowledge the elephant in the room.

“That way, when it comes up again from the audience you could say ‘Right. As I said earlier…,’ Millen advises. “Then you are reinforcing your answer and it feels more truthful and honest.” Also, you’ll avoid allowing an angry questioner to set the tone. “You can get it out there on your own terms,” Millen notes.


Sometimes a speaker is hit with a multi-part question and when that happens, the recommendation is to answer that part of the question you can answer most adroitly, the part that reinforces your viewpoint or supports your goal. Speakers can usually get away with this tactic because audience members may not remember the entire question and in fact, they may have little patience with a complicated question. So cherry pick those parts that you want to answer and slide away from what you are unable or unwilling to answer.


Unfortunately, there could be an audience member who doesn’t so much have a question, but an axe to grind or s/he is in search of attention. Jo Miller, founder and CEO of Be Leaderly, a professional development training consultancy based in Cedar Rapids, IA, cautions speakers against getting defensive when encountering such a questioner. “The best way to deal with those questions is to maintain a confident and unapologetic posture,” she says. Miller suggests that adopting a tone of amusement can help get the audience on your side. She adds “Respond as if you are enjoying a game of intellectual ping-pong.”


If you are a company leader who will speak to employees, investors, an important client, or others with whom you must build trust and meet or exceed expectations, bring along two or three ranking team members and have them ready to step in and answer questions aligned with their areas of expertise. In other words, defer to the experts, share the spotlight and promote leadership skills development as you do.

End the Q & A on an upbeat, positive note and if possible, after you’ve given a well-received response to a question. If you are asked two or more challenging questions, Millen recommends that you
“Tell them they’re asking the right questions, then bring it back to your overall message. They (the audience) shouldn’t leave with a bad taste in their mouths.”

Thanks for reading,

Image: Cesare Maccari 19th century fresco depicts statesman, lawyer and orator Cicero (January 3, 106 BC – December 7, 43 BC) as he excoriates Senator Lucius Sergius Catilina (108BC – 62 BC) in the Roman Senate for Catilina’s role in the conspiracy to overthrow the Republic and, in particular, the aristocratic Senate. Courtesy of the Palazzo Madama (Rome).

5 Customer Survey Questions That Work

Every once in a while, it makes sense to address your client feedback metric, so that you will receive some lived-experience insight into your operation’s strengths and weaknesses.  You need to learn what can be done better, which service delivery or other operational processes might be simplified and what clients would like to see more of.

The smartest way to begin the client feedback process is to decide what you want to know and what purpose that information will serve.  Are you trying to develop new products or services, so that you’ll be able to give clients what they want before they know they want it? Or is business dwindling and you’re in damage control mode, attempting to win back clients?

Some market research questions are best explored through the eyes of clients and others around the conference table with your leadership team (or maybe your front-line staff, who have loads of on-the-ground experience that they’d love to share). Let’s examine when it makes sense to query your clients and when you’ll learn more from in-house research.  Given below are five standard yet very clever survey questions, some that apply to clients and others that apply to you and your team:

  1. What are the challenges that clients (in a given industry or category) are facing?
  2. Which of these problems is our organization equipped to address?
  3. What solutions are we offering now and what can we/should we add, re-tool, or quit?
  4. How effective are our solutions—what do clients most often hire us to do?
  5. What do we do next?

Note that questions 1 and 4 would best be put to your clients and that questions 2, 3 & 5 involve business strategy and would be addressed in-house, once you’ve spoken with selected clients to figure out questions 1 and 4.

How you conduct the client survey deserves some thought, as well. It might be best for Freelance consultants and small business owners to run a low-key survey by setting up an environment that enables comfortable and candid conversation.  Consider making the process informal and perhaps even seemingly impromptu.  Larger companies may feel comfortable running a formal focus group, perhaps facilitated by an outside market research firm.

Question 1: What are the primary challenges facing your client’s organization?

Whether the client comes to you or you go the client, start by asking a “how are things going in your office” question, or inquire about the next big project or objective (whether or not it would involve your organization). Find out what’s going on and let the client talk.

Questions 2 and 3: Which challenges do you want to solve? How will that be done?

Given the expertise and resources you have, coupled with the client’s inclination to contract for the necessary billable hours, which additional client challenges might you be asked to take on (or what can you cleverly propose to be hired to do)? Can your organization successfully deliver the desired outcomes, or will you need to subcontract some portion? Can you learn how clients are managing these responsibilities now? Is there a competitor who gets hired to do that work , or is nothing being done because the client isn’t sure what to do, or lacks the budget to complete the job?

Question 4: Have our solutions satisfactorily resolved the clients’ challenges?

What project did the client hire you to do? What are the projects that your organization is most often hired to do? How does do clients feel about your performance—is your expertise and ability to deliver the service trusted and respected by clients? Does it seem that you’ll receive more business from several of your clients, on a similar project or another type?

Question 5: What do you do next, based on client responses?

Now here is the judgment call for you and the team. The essence of the process is interpreting the data compiled.  What can you realistically do, based on the responses from clients in questions 1 and 4 and the opportunities and strengths within your organization, as noted in questions 2, 3 and 5?

Remember, it is most likely possible to beta test a new or re-tooled service  with a trusted client who would receive a reduced project fee in exchange for helping your organization to perfect the business model.

Thanks for reading,




Getting and Giving Advice: Who to Ask, Frame the Question

We’re back with more thoughts and suggestions regarding how to navigate the matter of business advice, giving or receiving.  Previous posts have explored how to effectively give advice and the importance of using tact when advice is offered.  In this post, we’ll examine how to obtain business advice for ourselves.  As you might guess, it’s a delicate process.

Getting and Giving Advice: Skill Set

Getting and Giving Advice: Tact

First, if you are in need of advice, then there is either a problem or an opportunity that you must address (or ignore).  You are concerned and maybe even scared.  You are stressed and making decisions when stressed is seldom a good idea.  Stress impairs judgment and therefore increases the potential for an undesirable outcome.  Nevertheless, you recognize that another perspective could help you to sort things out. Who are you going to trust?

Yes, trust is a big factor when seeking advice. You must trust that person’s expertise and since confidentiality is likely involved, you must feel confident in the person’s ethics and practice of discretion.  You do not want someone who is unqualified to give the advice and neither do you want your private affairs indiscriminately shared.

Let’s start by helping you to identify a good advice prospect.  You may know more than one person who appears to own the experience and expertise that should make him/ her a good candidate,  but who should you approach?  Here are guidelines to assist your decision.

First, avoid asking someone who has competitive advantages that are significantly beyond your reach. If the person is prone to unusually good luck, or has a wealthy and influential family or spouse, then do not ask the individual for advice.  S/he may have built a highly profitable business, but because fate smiles on all of his/her endeavors,  s/he has faced no real obstacles.  Such persons cannot solve problems, because they’ve never had the need to do so.  They’ve never borne the consequences of either bad luck or their mistakes.

Second, look a little more at how the prospect has garnered  success.  Whether it was a fast climb to the top or slow, someone who has taken an unusual path has probably encountered an array of unexpected obstacles and opportunities that had to be conquered or exploited along the way.  Of necessity, that person has challenged assumptions, rethought the status quo and has the courage to move forward  when more conventional types might hesitate. As a result, that person has learned to be quite resourceful and could have real wisdom to share with you.

Next, confirm your advice prospect’s expertise in your area of need.  Just because someone has climbed the corporate ladder or built a million dollar plus company does not mean that the person is an expert in all disciplines.  A talent for strategy development is probably a strong point across the board,  but most people are strongest in either finance, operations, sales or marketing. Further, it’s been my observation that the intelligence possessed by computer geeks is very deep and very narrow, rendering them useful for IT questions only.  I would be reluctant to trust many of them to go the grocery store to buy bread and milk in a snowstorm.

Now, let’s consider the right way to ask for the advice.  As the late management guru Peter Drucker noted,  one will not find the fight answer unless the right question is asked.  Advice experts recommend that you NOT ask your prospect what you should do in your situation,  because s/he may get insulted if you decide to ignore their advice and follow another route.  Instead, ask if s/he has ever faced a situation like yours and if so, what did s/he do or say in response?

WRONG: “I feel that a big wholesaler is being unfair about the payment terms extended to me. What should I do”?

RIGHT:     ” Have you ever dealt with a big wholesaler who you felt was unfair about the payment terms extended to you? Were you able to do anything about it”?

Finally, you need access to your preferred advice candidate. It’s preferable to approach someone you are already acquainted with and that is the best reason for taking the time to establish business and social relationships.  The person who can most effectively guide you might be in the gym with you,  or at church, or at the lunch table at a symposium. Asking for detailed advice from someone you’ve just shaken hands with is awkward.

Ask your advice question, beginning with your clarifying question to verify expertise, in person if possible.  Your specific advice question can be asked in a follow-up telephone call if there is no time to address it on the spot, or if privacy is an issue.  Good luck!

Thanks for reading,




Smart Questions for the Client Interview

A Freelance consultant’s first project specs meeting with a client or prospect is the time to start building the foundation for a successful working relationship.  A major element of a positive and productive relationship is your understanding of the client’s priorities,  which will allow you to assess what will be required to meet or exceed expectations.

Are you capable of doing the job alone, or must you subcontract some portion to a Freelance colleague ? Can you successfully complete the project within the client’s preferred time frame?  What will be your project fee or hourly rate?

Asking the right questions guarantees that you will receive the information that you’ll need.  As the meeting proceeds,  be sure to ask these three questions.  Your client will be happy that you did.

  1. What do you expect me to accomplish in the first 90 days?

Freelance consultants must hit the ground running. Unlike salaried employees,  there is no training or orientation period.  Often,  there are certain components of a project that organization leaders deem more critical than others. These components could be the most time-sensitive,  or simply the most urgent problems. If there are any front-burner issues,  you want to be prepared to take them on straight away.

     2.  What do you see as driving results for this project?

Getting your arms around these matters can make your project work easier and ensure that you achieve all milestones within the preferred time frame.

      3.  How does this project fit into the organization’s highest priorities?

Seeing the big picture is always helpful.  How important is your project to the company’s long-term strategy and mission-critical goals?  Your pricing will also be impacted by this knowledge. If the project is pivotal,  the smart Freelancer charges a premium.

Within 24 hours after the meeting,  send an email to confirm all major issues and agreements requested by the client and yourself  (think scope of duties,  milestones,  deadlines and your payment schedule). Your email can constitute the project contract and it has legal standing.

If your client would like you to perform additional tasks along the way, confirm that request, including the completion timetable, in writing and specify the additional fee and the payment due date.

Thanks for reading,


So Why Should They Hire You?

Congratulations! A client with a big budget and a need for your kind of services has called you back for a second talk. You’re excited and a little nervous, too. There’s a lot riding on this interview—maybe this is a prestige client who will help you attract still more prestige clients? Maybe you have bills to pay and this assignment is your ticket to solvency?

Whatever your motive, acing the interview and signing the contract are paramount. Then the client throws this last-ditch, totally common and yet potentially flummoxing question at you–“Why should I hire you for this project?”

Most of us will flap our jaws aimlessly, talking about the value-added we bring, our work ethic, excellent customer service or deep expertise. All of these benefits are positive but in today’s hyper-competitive economy, a Freelancer must make a stronger case. We need to make the client salivate to have us on board.

As luck would have it, there are some good stock answers available and they will make you shine. These templates give the prospect the confidence to open the door and bring you onto the team. You maximize the impact by replying in a relaxed tone, keeping your answer clear and simple and avoiding the use of jargon.

Interview coach and author of Convince Them in 90 Seconds (2010) Nicholas Boothman suggests that you try something like this… “You know how an outside specialist has to be flexible and ready for the unpredictable? Well, I know how to adapt to changes, I have initiative and I can cover a lot of bases, so your team members will be able to concentrate on what they do best and I can take care of the other stuff that needs to get done.”

You might also try something suggested by business journalist Geoffrey James, author of Business Without the Bull (2014)…. ” You know how sometimes you can’t find top talent to bring on when you need them most? Well, I have ( x amount of) years experience in (whatever field) that will let me solve your (problem or need) and get the right solution up and running in a short time frame. When you hire my organization, you won’t have to spin your wheels searching for talent and you’ll avoid the risk of hiring the wrong person.”

Here’s a cool little retort for the Freelancer who has not seen age 35 in a few decades and it works whether one is speaking to a Baby Boomer, Gen X, or Millennial…”You know how sometimes people can get into emotional battles over how to approach a problem? One of the most important things I’ve learned over the years is how to bring these kind of conflicts to a quick resolution. If I’m on your team, you’ll not only get an experienced (name the specialty), but also someone with perspective, who can guide a team away from butting heads and toward getting the work done.”

Note that your answer positions you as the solution to the client’s problem or need and that is precisely how you want to be perceived, for that is why you will get hired. You may devise other answers that more closely reflect the circumstances of your field. Anticipate the question in advance of your next client meeting and think of scenarios that will help you answer the “Why should I hire you” question in a way that focuses on the client and how you can make his/her life easier.

Thanks for reading,


Prospects and Tire-Kickers

Tire-kickers, those self-absorbed time-wasters who parachute into your life, present themselves as interested buyers, pepper you or your sales staff with questions, raise red-herring objections and then slide away without spending any money. Freelance consultants, business owners and sales professionals regularly contend with “prospects” whose mission in life, it seems, is to squander others’ valuable time. Tire-kickers feel completely entitled to mislead honest working people by feigning interest in products and services that they have no intention of purchasing any time soon.  They also get their jollies by inviting marketing consultants to meet for coffee and discuss projects that have neither official support nor budget.

Tire-kickers are the bane of a Freelancer’s existence.  A method to politely expose and dispose of them is a useful time management skill. Posing questions and raising objections while in the buying process is responsible behavior and all whose livelihoods depend upon making a sale welcome serious prospects, including those who do not buy at that time. How does one tell the difference between a tire-kicker and a prospective customer? It all starts with asking the right questions (but you knew that).

The Zero Pain Hypothesis developed by Liz Ryan, founder and CEO of Human Workplace, assumes that a caller has no need for what you sell and it is an effective template to follow. Keep your tone friendly and helpful throughout. You might be able to persuade the tire-kicker to either make a purchase in the near term, or make a referral to a colleague who has money and motive to do business with you now.

1.  Who?

To whom are you speaking? Get the name, title, company, phone number, email and location of the person who makes contact. Get qualifying info up front and begin to make that person commit to the buying process. Questions are cheerfully answered, but this is not a game, it is business. The job title can help you know whether this person is likely to be the decision-maker or key influencer.

2.  What and Why?

What is the product or service that is being investigated and why is it needed? What business imperative is a priority for the caller? If the caller can provide a logical reason for contacting you and/or describe what has been done that is not  working, then you probably have a genuine prospect. The counter-intuitive genius of the Zero Pain Hypothesis recommends that you offer up an inexpensive, maybe DIY alternative to your services. Tire-kickers should back off once told of a cheap and easy path to what they want. As well, tire-kickers will reveal themselves by their vague and evasive answers to your questions.

3.  When?

Assess the urgency. Is there a deadline for completing the project or making the purchase? If things are open-ended, then you are speaking with a tire-kicker. The Zero Pain Hypothesis recommends that if possible,  you recommend a “place-holder” alternative, an inexpensive band-aid that will help out for the short-term, since there is no defined timeline.

4.  Where?

Where is the organization in the buying process — early stage vendor list making, soliciting proposals, or close to finalizing the decision? Is your questioner the decision-maker and who else may need to weigh in? What is the budget? If the caller has a deadline and/or a budget, then you probably have a genuine prospect. If the caller’s budget does not meet your minimum, then refer back to the cheap alternative. Restate what the project or product means to the caller’s business. If something big is on the line, that person might be able to perceive the “pain” point that your qualifying questions encourage him/her to acknowledge and proceed to talk him/herself into increasing the budget and selling him/herself on the value of your services.

Thanks for reading,


12 Sample Customer Survey Questions

In numerous posts over the years,  I’ve recommended that you conduct customer service surveys to guide your decision-making as you refresh your brand,  update your business model,  promote client retention,  stimulate referrals or initiate any other changes in your business practices.  Customer surveys can unearth all sorts of interesting and actionable data.  A dozen well-written questions can  give revealing insights into what drives the need for your services,  what persuades decision-makers to choose you instead of a competitor and customer expectations that may not be immediately apparent.  Surveys help you learn how your operation stacks up against the competition and can identify business strengths and weaknesses.

To give you inspiration,  I hereby provide a few sample questions.  Send your customer survey along with the final invoice of a project.  Include it on your website,  Facebook, Google + or LinkedIn page.  Announce it on your Twitter feed.

  1. What service did (the company) provide for you?
  2. What factors made you decide to hire (the company) for this project?
  3. Do you feel that your project contact/manager acted in your best interests and your organization’s?
  4. How closely did (the company) adhere to the agreed-upon project timeline?
  5. Do you feel that your project contact/manager responded to your requests for information and other inquiries in a timely fashion?
  6. Considering the value of this project to your organization,  how do you feel about the amount paid as compared to the value received?
  7. If you feel that you received poor value,  please describe the problem (s).  How do you feel about the process of providing resolution?
  8. Would you be willing to invite (the company) to work with you on another project?
  9. Are there additional services that you wish (the company) would provide?
  10. How often do you typically hire outside project-specific workers?
  11. Based on the experience of working with (the company) would you be willing to recommend to a friend or colleague?
  12. Do you have any suggestions for improving the services provided,  or related administrative matters?

Thank you for your feedback. Your honest opinions are sincerely appreciated.

A big part of growing a successful business is through referrals and repeat business.  Clients only return to you or recommend your services when they are extremely satisfied with your performance and have a high degree of confidence in your operation.  Your clients possess a wealth of information that may not only give you the opportunity to bring solutions to their problems and increase your revenues as a result,  but may also give you ideas about how you might attract new business.  The only way to access this information is to ask your clients and listen to their answers.

Thanks for reading,


Smart Sales Call Questions

Management guru Peter Drucker famously noted that in order to get the right answers,  it is first necessary to ask the right questions.  Whether the subject is love or money,  many of us do not ask direct clarifying questions because we are afraid of the answer.  It takes courage,  sometimes,  to hear the truth.  But in the end,  only the truth is useful. 

I recently found this list of sales call questions and they are a little scary because they cut right to the heart of a prospect’s motive and let you know what is real and what is not.   I vow to pose these questions in my next sales call because it is far better to know  what I’m dealing with.  Time is much too valuable to waste trying to wrestle an assignment out of a prospect who does not have the means or real motive to hire me.  Write these down and post them at eye level:

1.  In terms of time,  money and/or risk,  what business problem will working with me solve for your organization?

You’ll learn the reason the project is out for hire and assess your ability to do the job.  You’ll  learn whether or not there really is a project,  or if the prospect is merely checking out available talent.  Maybe the prospect only wants to compare the Freelancer they usually use to who else is out there?  If there is not a genuine problem to resolve with a timeline and budget attached,  then your prospect is only window-shopping and there is no contract here.

2.  How will you measure success 60 days after we begin working together?

The answer clarifies the goals and objectives you must meet if you win the assignment and also identifies the metrics that will be used to measure your progress as you work.  You’ll confirm that milestones and metrics have been set for the project and that it is real.  The prospect’s  seriousness and sincerity  (or lack thereof)  will be demonstrated in the response.  You will understand how you will approach the project and reconfirm whether you can meet expectations.

3.  How much better does my  “better”  have to be for you to bring me in on this project?

The prospect’s answer will reveal if he/she knows what they’re looking for in terms of whom to hire as a Freelancer.  Are the expectations reasonable in your opinion and do you have the wherewithal to meet them? Might you have to call in a subcontractor to meet a special demand or timeline?  You can assess the level of interest in your services and determine if you are a contender or merely filling out a list that must contain a certain number of names.

4.  How soon do you need to see progress or improvement for you to know that you’ve made the right decision in hiring me for the project?

Once again,  the prospect will show that he/she has thought things through,  has established clear and reasonable goals,  objectives,  timeline and metrics and recognizes success.  You’ll have another means to confirm that the project is real and there is something for you to pursue.

5.  What process will you follow in bringing me on as a provider of this service?

Process questions reveal how far ahead your prospect is thinking.  This question will demand that the prospect envision hiring you and think through what must be done to bring you on.  What budget is available and who else must sign off on your hire? If your prospect has only a fuzzy answer to this question,  then he/she may not have the authority to hire you.

Thanks for reading,


Your Sales Pitch and What the Client Thinks About It

Selling is a huge part of a Freelancer’s job,  because we don’t survive if we don’t sell someone on the idea of hiring us.   In other words,  a Freelance consultant is a salesperson first and foremost,  regardless of the services we provide.   We must keep our selling skills razor-sharp and be forever mindful of what a prospective client needs and wants.

Before you waste time making some grandiose presentation in your next prospective client meeting,   put yourself into the shoes of the person or team you’re trying to sell.   Because you’re in business too,  you know that every day  (or so it seems)  someone is trying to sell you something that you probably don’t need.

Take this reality test first.   Whenever you buy or sell anything,  ask yourself  these three questions,  which will be approached from your personal point of view when buying and from your prospect’s point of view when selling:

1.   What do I need this for?

2.   Why do I need yours?

3.   Why do I need it now?

These are simple and uncomplicated questions,  but they’re not always easy to answer.   When you can convincingly address these questions from the client’s perspective,   I guarantee that you’ll be able to sell them  (assuming that they have the budget).   This exercise forces us to a deeper,  less self-absorbed way of thinking about what we sell and how we sell it and will  result in a more effective sales presentation.

The first question,  “Why do I need this?”  forces the seller to expertly define the value proposition.   In the pre-sales meeting discussion,  ask questions that will help you understand why you’re being invited to meet with this prospect,  what the pressing needs and hot buttons are and what the client may be worried about.

Understand the objectives and how whatever it is you do fits into the big picture.   Begin to understand how what you offer can successfully achieve those objectives and ensure realization of the big picture goal.   Then,  figure out how to express the value of what you bring in language the client will understand.

The second question,   “Why do I need yours?”  is when the seller describes the unique differentiators,  the competitive advantages.  What would make the prospect pay you to supply this product or service?   Here is where we describe that which sets us apart,  why we’re better than the rest,  why it makes sense to go with us.  Answers to this question are formed in bullet points.   They are crisp and clear,  easy to express and remember.

The last question,   “Why do I need it now?”  is the most important of the three.   Here is where the seller states the most compelling  drivers—the need,  pain,  opportunity,  event,  etc.,  that will cause the prospect to make the decision to use your product or service and commence the buying process immediately and not at some yet-to-be-determined point in the future.

This question makes us think seriously about prime motivators and how to eloquently and succinctly express them to the prospect and make him/her want to do the deal right now.   Is the need for your product or service an immediate priority?

If you’ve taken the initiative to approach the client rather that the other way around,  you may find that you’re ahead of the curve,  that you’re presenting a course of action that the prospect isn’t prepared to take,  that he/she hasn’t yet bought into.  If that is the case,  you will have a long market education cycle ahead of you and may well end up empty-handed.   Conversely,  you may learn that you’re too late and the need for your solution has passed.

Nevertheless,   however you mange to get yourself in front of a prospect,   answering these three questions first will serve you well every time.

Thanks for reading,