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Managing Up – You Can Never Ask Too Many Questions

Avoiding the Expectation Trap

By: Stan Tilton – June 1, 2016

I was recently retained to coach a young fast-tracked employee at a premier New York manufacturing company. I shall call the coachee Anna. She was recently promoted into a challenging position, where her predecessor abruptly left the company after only six months in the job. Anna reports to the new Marketing Director who was a high profile recruit by the company, who I shall call John. Anna’s personnel file included two announcements regarding separate promotions she received in less than four years at other company divisions. In addition, Anna’s resume includes an MBA from a prestigious East Coast University with a nationally ranked Graduate Marketing Program. A recent annual performance review, given by Anna’s previous manager, rated her 3.5 on a scale of 4.0.

The company’s HR Manager informed me that everyone was surprised when it was learned Anna was having performance issues by not meeting her new boss’s expectations. I was told Anna is smart, while maybe introverted, she is still considered proactive and engaging. She is known to have high energy, meticulously hard working and friendly and she had favorable ratings on each of the company’s pre-hire assessments. Further, her two previous managers told HR that Anna had earned a reputation of meeting or exceeding expectations.

During my first meeting with Anna, I asked what she knew about coaching and if she knew why I was asked to work with her. Without hesitation, she told me that she has a problem with her boss John, and that she has made many attempts to professionally connect with him. She has been frustrated by her inability to understand his personality, and she hasn’t been able to communicate her displeasure with his delegation style. Her attempts to commutate with him have fallen on death ears. She said John gives her little or no training in her new job and insists he never gives clear instructions on when her assignments are due, what his expectations are or how she will be held accountable. She told me, while she hasn’t worked with a coach before, she understands coaching because she knows two colleagues who were coached and they spoke favorably about their experiences.

Prior to starting my work with Anna, I spent time with her boss, John. I found him friendly, confident and professionally engaging. He told me he had high hopes for Anna and that she was promoted into the current job because of a recommendation from her previous manager. John told me that he was dumfounded as to why Anna almost never meets his expectations and that he has no choice but to hold her accountable for her failures to perform. He went on to say that unless she soon figures it out, he will be forced to ask HR to reassign or terminate her. He told me that I have six months to get her straightened out and performing to his expectations or she’s gone. John concluded our conversation by saying he does not believe in executive coaching, but HR talked him into it.

Armed with the history supplied by HR, John and Anna, I conducted a 360 Degree Feedback Interview Process with ten colleagues selected by Anna and approved by John. I interviewed a good mix of employees, which included John, Anna’s prior boss and two other colleagues from her prior division and finally some current peers of Anna and ended with John’s immediate superior.

To gain a better understanding of why Anna felt she was not being treated fairly by John, I had several background history and probing discussions with Anna. She told me she can never do anything right for John, she hates calling or going to his office for fear he will blow up and dump on her about what he considered her many faults. She doesn’t trust him. She shared with me that he once asked her, “why do you want this job, you don’t appear to get it?” She further shared with me that she was at the end of her rope with John and if the coaching doesn’t help her figure things out, she would most likely quit the company or ask for a transfer.

In one of my early coaching sessions with Anna, I asked her to give me an example of an encounter or situations she thought would demonstrate her troubling experiences with John. She told me about a project John assigned to her.

As I understood the project, Anna was instructed to research and analyze reasons why a major product had considerable sales slippage in the recent quarter. John told Anna that he believed the drop in sales was the result of losing long standing customers. She was instructed to interview at least 50 inactive (lost) customers, analyze and interpret the results and then write a report of her findings, which he would pass along to management. Anna indicated she specifically asked John what kind of questions she should ask during the interviews, were there any specific past customer profiles he had in mind for interviews and finally how he wanted the report organized? Anna said she pressed John on those questions as well as when the report needed to be completed. She said his only response was “I have complete confidence in you, just get on with it.”

Believing John gave her a vote of confidence, Anna started the project. I asked her how she went about conducting the project. She told me she consulted with customer service and sales personnel as she developed a cross section of former customers. Drawing from her past college courses on market research and analysis, as well as her experience gained at other company divisions regarding the company’s typical report formats she believed she knew how to accomplish the task assigned by John. She told me she thought the project would be a “piece of cake.”

Anna insisted she conducted her research with a methodical and focused approach, similar to how she worked on past projects at the company. She even sent John an early update on how the interviews were progressing and a second email 30 days later with a draft of her findings. Neither email to John drew a negative response; except for an innocuous comment not to forget to include certain minor customer history items in her report. Believing John’s short responses were good news and absent any negative comments, Anna was confident she must be moving in the right direction and continued pushing forward with her interviews and fine-tuning her draft of the Market Research Report.

Then one day, unexpectedly John walked into Anna’s office, appearing angry and frustrated. Anna knew something bad was up. John greeted her with “I don’t think you get it, you are making me look bad”.

Stunned, Anna said “how do you mean?” According to Anna, John retorted, “the report, where is the stinking market research report? I need the report now.”

Anna quickly printed her current draft. Not understanding what was causing John’s noticeable angst, she thought once he saw the substantial work she put into the assignment he would certainly calm down and be pleased by her excellent research and report writing skills.

While John was looking over Anna’s report he burst out, “what is this, this is not what I wanted.” He said, “why did you only interview 50 past customers? I told you at least 50…meaning more. I don’t like the format and besides, it’s late. Why is it so late?” He said, “if you didn’t know what you were doing, why didn’t you ask me for help?”

Bewildered, Anna replied, “I did what you asked for, sent you a couple email updates and a draft report, and you never told me it was not what you wanted.”

John snapped back, “a professional would know what I wanted and I expected you to bring something above entry level work to the table.” He added, “I expected some creativity and thinking outside the box.” He sniffed, “this is not it!” “I have an open door policy and I never saw you once at my door. You never asked me what I wanted and now you wasted so much time. I will have to finish it myself.”

Based on everything I understood about the relationship between John and Anna, I believe she walked into a classic failed delegation and resultant expectation’s trap. John, the boss failed to give Anna, the subordinate, detailed instructions on the project. John failed to tell Anna the scope and how to go about doing the research, and he failed to tell her the report format he wanted. Finally, Anna’s boss failed to tell her the date he wanted the work completed. Conversely, Anna, the subordinate, failed to initially ask enough qualifying or clarifying questions necessary to completely understand what was being assigned to her and she failed to insist her boss tell her the due date for the final report. And over the course of the project, Anna failed to specifically ask for feedback on her progress and she failed to ask any mid-course guidance questions.

Where to place blame for this communications disconnect was not what the company wanted from me. Perhaps that would be for another day. I was charged with coaching Anna to succeed in her current position by helping her to learn managing up. This was my assignment, notwithstanding John’s apparent failure to manage and delegate effectively.

Anna is dealing with a boss that is apparently a poor communicator, who is not precise in providing instructions, responsibilities and expectations, fails to give guidance and most likely gives little or no training to his subordinates. Further, John never gave Anna the date he expected her work completed. Anna, perhaps because of her introversion and/or youth, failed to ask the necessary clarifying questions to meet her boss’s expectations. In Anna’s mind she preformed her task as she understood and in John’s mind she failed to do her job and she needed to be held responsible.

Given the company’s investment and future expectations for John, who is considered a valuable new key member of the executive team, as well as his history of producing stellar results since joining the company, it’s unlikely John will be seen as the possible cause for Anna’s perceived deficiencies.

It’s important to note that a question included on Anna’s 360 Degree Feedback dealt with how well she meets expectations. I was not surprised when seven of the ten respondents said Anna was being set up to fail; she can never meet John’s expectation, because John doesn’t know how to effectively delegate and he sets traps for his subordinates. I was told by more than one respondent John expects and demands his people to sink or swim. He will always tell you what he wants, but never gives you any details or define his expectations.

During my feedback interviews I asked each of the respondents that raised John’s delegation issue, did you or anyone you are aware of bring to John’s attention that he has a reputation to unwittingly set traps because he can fail to inform people of his expectation? Their collective answers surprised me, the consensus was summed up by one interviewee’s comment “you don’t tell John anything, he knows it all and expects his people to figure it out themselves.” Another participant said, “When you do what you perceive John wants and you don’t deliver to his expectations, he blows up, rips your head off and says you failed.” A number of Anna’s colleagues told me they pity anyone that has to report to John. One suggested I should look to the past, the last person in the job quit in only a few months.

When I updated HR regarding my progress with Anna, I asked again if they were aware of any management issues that may be complicating Anna’s assimilation into her new marketing role. I was stunned when I was told, “yes we know all about John, but John is a super star and on a fast-track to the top. The company has a substantial investment in John. He has been told about some of the company’s concerns about his management style, but John knows himself best and does not believe he has any issues requiring his attention.“ Further, I was told, “he expects his people to do their job and shut up. I was told the company does not wish to deal with John at this time.” The HR VP said, “since John is relatively new, people just need to get to know him better and understand how he operates.” I was advised Anna is the person that needs coaching, so let’s not worry about John. In fact you should know John was surprised when Anna asked to participate in the coaching program that was recently made available to employees at her level. He does not believe in coaching and has declared it, “a waste of company money.” But because of Anna’s past successes the company has decided to continue investing in her by providing her the coaching program.

As guidance to avoid an Expectation Trap I offer the following tips to Manage Up:

  1. Don’t assume anything. Always ask qualifying questions up front and throughout the project or assignment. If further questions arise during the project don’t proceed without asking more clarifying questions. You can never ask too many questions. It’s easier to make mid-course corrections instead of waiting until it’s too late.
  2. Just because you had success at a past job, don’t assume things are done the same way in this job or for this boss, even in the same company. Always ask your boss to give you detailed instructions. Don’t be embarrassed to ask as many questions as necessary to understand the project or assignment. Don’t hesitate to email your boss spelling out your understanding of the project or assignment, expectations and due date. Ask for confirmation.
  3. Check with colleagues regarding your boss’s behaviors, quirks and methods of managing and doing things.
  4. Keep your boss informed and in the loop. Never surprise your boss.
  5. If you encounter problems, stop and ask your boss for help to solve or suggest a workaround solution.
  6. Ask for project or work assignment completion dates.
  7. It goes without saying, always perform your job to the best of your abilities.
  8. Practice the above tips and you will stay out of an expectation’s trap.
  9. By staying out of the trap you will enjoy a job with considerably less stress and without fear of being held accountable for any unintended or unforeseen consequences.
  10. For additional tips see my recent post “Using ‘Ideas’ to Manage Up,” which defined my managing up formula to Inform, be Direct, Engage, be Assertive and never Surprise your boss.
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