Is Your Ask as Good as Your Tell? Perfecting the Art of the Ask

“Shyness is nice, and shyness can stop you from doing all the things in life you’d like to. So, if there’s something you’d like to try, if there’s something you’d like to try, ask me, I won’t say no, how could I.”

Lyrics from the song Ask, The Smiths (1986)

If You Don’t Ask, The Answer Is Already No

Several years ago, one of my best friends had recommended the movie 500 Days of Summer which I have now seen multiple times and the movie soundtrack is now one of my favorite of all time, especially a couple of great tunes from a popular British band from the 1980s, The Smiths. As so often is the case with my love of music, once I find a new artist or a song that I really enjoy, I invariably go to the iTunes store to search for other great songs from that artist — that’s exactly how I stumbled on their catchy tune Ask that I referenced above. 

Last week as I was doing my power walk in beautiful Mill Valley, CA, I found myself thinking anew about the inherent message of this song’s lyrics. My sense is that many of us never get truly comfortable asking someone else for help, whether we know the person or not; rather, it just seems easier if someone asks us for our help, especially when it’s involves a member of our family or a good friend. When someone asks us for something, it can often engender a heartfelt response like “thanks, I was hoping you would ask me”. Even in situations where we might initially hesitate in saying “yes” to a specific Ask, once we accept an invitation, it can often lead to a positive experience. There’s even a spiritual dimension that one can associate with the very concept of asking and its found in Luke 11: 9-13 “Ask, and it will be given to you; seek, and you will find; knock, and it will be opened to you. For everyone who asks receives, and he who seeks finds, and to him who knocks it will be opened”. 

Having the courage to Ask for someone’s help or the courage to say yes to someone’s invitation asking for your help can be truly transformative experiences, but most of us probably have a harder time when we are the ones doing the asking and for a variety of understandable reasons. First, there’s the fear that some people might perceive us as weak for the Ask; secondly, there’s the very real fear of not getting the response that we are hoping for from the person we are reaching out to or worse yet, not getting any response at all! Finally, Asking someone for their help on something can also make us feel vulnerable. 

As I continued my walk, I began to think of moments in my own career where I wasn’t as fully prepared as I could have been in Asking the right set of questions about a project that I may have been working on or for pursuing some of the potential opportunities that I was interested in either inside or outside the various organizations I worked for. Perhaps as the song’s lyrics suggest, I was too shy to Ask or simply lacked the self-confidence to Ask the appropriate questions to either my superiors or direct reports which may have impacted my own job performance or career arc.

Most of Us Focus Our Time Preparing The Art of the Tell 

At Kirnan Coaching Associates, LLC, I spend a lot of time helping clients perfect what I refer to as The Art of the Tell and what in the mid-1980s we used to call the Elevator Speech. Every Tell or Elevator Speech is unique to each client and is a strategically scripted statement of what their unique value proposition is to a prospective employer in a job search campaign. It is continually tested, refined, and honed to help the client without any hesitation or pretense answer that common question that comes up in an interview — “So, tell me about yourself, Jack”? The script’s central character is the client whose underlying theme is one of clarifying specific accomplishments and skill sets that frame the backstory of their career to date and how they hope to use that portfolio to create their next new chapter. When a client’s Tell is aligned with a polished resume and a well-developed LinkedIn profile that includes the critical keywords for the job targets that have been identified, it can truly be THE significant factor in a successful job search campaign.

Perfecting The Art of the Ask

An equally important factor in a successful job search campaign is learning The Art of the Ask, which can be particularly challenging for clients during the early stages of transition. As I often say to my clients, if you can’t get comfortable Asking someone for what you want during job search, then the answer to your question is already NO! So, if clients can get comfortable in developing The Art of the Ask, then the people they reach out to during job search just might say YES to whatever their specific Ask might be. 

Here then, is a framework that can help you develop The Art of the Ask as you navigate your professional network as well as the companies and functional areas of interest that appeal to you.

Know What to Ask:

  • Always be clear, concise, and upfront on your specific Ask! What is it that you want from the person you are targeting. For example, in job search, maybe you are going to ask someone in your professional network for their help in arranging an introduction with someone you’d like to connect with at one of your target companies. Make sure you are upfront as to why you want to meet the target so that the person acting on your behalf can make it easy for that target to respond favorably to your request. 
  • Sometimes your Ask might involve something outside of job search like soliciting input from people on a project or a proposal that you are working on. In your solicitation, make sure you are specific about how much time might be required on their part and a date and time for when you’d like to receive back their response. Providing that extra clarity will increase the chances for getting your desired response.
  • For any Ask, always search for the common connection between you and the person you are reaching out to by reviewing that person’s LinkedIn profile. The more you can identify what that common connection might be, the more productive your conversation will likely be. This is particularly relevant when you are in job search mode. 
  • In framing your specific Ask to your target audience, always provide specific options on how best they should get back to you. For example, should it be through email, text message, a phone call, grabbing coffee, etc?

Know How to Ask:

  • Deliver your specific Ask in as many different platforms as you can, either directly by phone call, email, text message, and LinkedIn messaging, or through various social media platforms like Twitter and Facebook. Ideally, any Ask should be positioned in whatever communications platform provides you with the best chance for a timely response. 
  • Practice your Ask as much as possible, always looking to refine and perfect it as you receive feedback from the people and organizations you are reaching out to. The practice will really pay off in the same way that shooting 100 foul shots a day as a youngster improved our performance on game day. 
  • Whatever your specific Ask may be, don’t be afraid to hear the word “No”! Always remember, if you don’t Ask, the answer is already No, so keep on asking.
  • The people you Ask have busy schedules so if you do not get a timely response, it’s not necessarily about you. And, it’s okay if you Ask your professional network and targets more than once! Keep moving through your list of people to contact expeditiously, always with an eye for adding someone new who can help you in your search efforts.
  • Employ small group (micro) emails where appropriate because often asking multiple people on an email will invite a timelier response and encourage others on the email chain to respond as well. Micro group emails can enhance the overall conversation and be helpful to others on the email chain with any information that is shared within the group. 

Know Who to Ask:

  • Be selective and targeted as to who in your professional network you will reach out to with your specific Ask. Logically, the people that you target, should be aligned with the specific job targets you have chosen for your search campaign. Always search for professionals in those companies, industries, and functional areas as well as the specific job titles that are of greatest interest to you. If you are trying to change industries, look for LinkedIn profiles where the professional has successfully transitioned to a new industry or functional area that’s of interest to you. Identifying those types of profiles can be of enormous value to you in your search. 
  • Once you have identified your targets for a specific Ask, begin your outreach efforts with the easy calls and the people in your professional network that you know best. It will help build up your self-confidence to make those more difficult calls that fall outside your comfort zone.   
  • Follow through each Ask you have with your network and new targets with gratitude. Expressing gratitude will increase your confidence to Ask them again should another situation arise in the future. It also makes it easier for you to inform them of your progress on the specific Ask and/or share with them items that may be of common interest like an article you came across or an interesting conversation you may have had with someone else in the field. Make sure you also Ask them “Who else would you recommend that I talk to?” This question will often unleash a whole new set of potential targets that you can connect with that is related to your specific Ask

As my good friend, Tom likes to remind me and my Cornerstone brothers, there are lots of people who are just waiting to be asked and to be of help to you whatever your specific Ask might be. And, many of the blessings we receive in our life and career come either because we had the courage to Ask someone or say YES to someone else’s Ask. So, take some time to learn The Art of the Ask — it’s a skill that can be perfected with practice, patience, and careful thought. Perfecting The Art of the Ask, especially your unique Ask –might just open some new opportunities for you and help you get closer to what you really want. 

With Best Wishes and Blessings to my clients and colleagues, 

Dr. K

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