Risky Business

 How to Know When (or When Not) to Take Calculated Risks.

The sun was shining brightly one beautiful summer morning, not too long ago. As I approached the breakfast spot where I was meeting one of my mentees, Alice, I happily anticipated connecting with her. Alice is very passionate and fun loving and she always puts me great spirits. I expected our time today to be like always.

Alice arrived and joined me at the table. After making some small talk about our families and recent vacations, it was time to begin our session. A very focused and action oriented individual, Alice usually had an agenda or items she planned to discuss. But not today. ‘How strange,’ I thought. Furthermore, she didn’t seem to be acting like her normal self. I wondered what could possibly be wrong.

Alice opened up the conversation. Like a cannon ball, she fired out the sentence: “I received a bad review for the first time in my life.” Her watery eyes and shaking voice punctuated the gut-wrenching impact. Then, silence.

I knew to give her a moment to compose herself and gather her thoughts. But after about two minutes, I thought maybe I should start asking her some questions. Three minutes went by. The fourth minute of yawned on. I finally determined that she needed to feel absolutely comfortable to share so I decided to be there with her as long as it took, no matter how uncomfortable the silence was. After about five minutes, Alice finally continued.
Alice is responsible for a department of about 5 employees. Her team works with external clients to deliver on projects. As the manager, it is her job to assemble and assign the best team of talent for various client projects. On one particular project, she didn’t have any internal team members available with the right skill set for the job, so she had to rely on a contractor.

Among her options, there was one individual who would be able to provide content and design for the client. An added bonus, this person had previously worked with the company. The only caveat is that this person had a history of conflicts with some employees. Alice presented her options to her boss, who was aware of the consultant’s past negative interactions. Alice’s boss cautioned her that this consultant might not be the best choice of partners and further encouraged her to reevaluate whether the project truly required external help. Alice made the case that contracting the outside help would be great for displaying the company’s capabilities. Additionally, Alice projected that if they did a great job, the client would award them more business. Alice’s boss left the final decision up to her, so Alice proceeded with her plans.

Alice was confident that if she had an open discussion with the contractor, they might be able to establish appropriate boundaries and have a good working relationship. When they spoke, Alice acknowledged that not everyone gets along and sometimes there might be personality conflicts. She positioned herself as an advocate for both the contractor and the project, believing that with a careful working relationship, everyone involved – the contractor, the company and the client – would all be able to experience success. With the positive indications she received from the contractor, Alice felt strongly about proceeding with hiring her.

The multi-phased project was slated to be completed in 8 months. Initially, things started off well. Alice, with multiple other projects to manage and not having the right skill-set for the project, relied heavily on the contractor for her expertise. As the project moved into the second month, Alice began noticing a trend: the contractor never met a deadline. She always had a seemingly valid reason for not producing her deliverables in a timely manner. Alice was starting to get frustrated and had a conversation with the contractor who assured her that the work would get completed.

Not all experiences with this contractor were bad. When it came time to put the technical infrastructure in place for implementation, the contractor had recommended a particular tool. Alice, not knowing much about it, took the suggestion to her internal technology team. The team investigated the solution and determined that the contractor indeed had made an excellent choice.

In spite of the few bright spots, the project still proceeded with problems stemming from this contractor. The issues were no longer isolated; they were beginning to compound. Alice had a meeting with the contractor 8 weeks away from the project deadline and learned of many issues which were going awry. While the contractor had recommended usage of a critical tool, she didn’t have any previous experience with it. She was just learning how to use it as the project was going along and was creating a lot of errors in the process. Alice also learned that detailed conversations she thought was being conducted with the client were in fact very general; critical information for the project had not been captured.
As Alice continued recounting the story to me, she began to cry. I tried to comfort her by letting her know it was ok to make a mistake if she learned from it. But Alice said that wasn’t all. Alice had one of her colleagues to review the project and it was determined that the project is not going to be delivered on time.

“I have a way to fix it, but it costs more money and am going to have to ask for more time. The project will be delayed by 2 months.” Alice expressed feeling mortified over the impact having a delayed delivery was going to have on the company. She never intended to hurt her company’s reputation in this process.

I felt this was a good point in the conversation to begin to examine the various issues packed into this problem. First, I pointed out that there is nothing wrong with taking calculated risks. The key, though, is to always have a backup plan from the beginning. Next, we tackled the fact that she was advised against working with this particular contractor but decided to move forward anyway. Alice ignored her own instincts and red flags which she saw along the way. Alice didn’t have a plan for handling poor performance with this contractor.
Another area Alice could improve is having a better system for staying on top of projects in process to insure key milestones were being met at the designated points in the project time line. Here, Alice could have put together a team across the network of talent to work with her and the consultant; she could have shared the work load and avoid creating a bottleneck in the workflow.

Risk is a part of life and certainly a part of business. It would be nice if we could roll the dice and always hit the jackpot, but that is unrealistic. The best we can hope for is to forecast various scenarios for a situation and be ready with an appropriate plan of action to implement that would likely lead to the desired outcome. When working with others who have established a reputation for themselves (particularly a negative one), it is important to always “reading between the lines” and properly identify and address red flags. These red flags will reveal potential areas of impact and the opportunity to change course.

Acknowledged as a “visionary leader”, Vicki Hamilton develops new IT strategies to address old workplace problems. An award winning technology executive with over 20 years of senior level experience, Vicki’s strategies drive high value results ($20M+.) Her latest initiative, The Wright Answer, is a global online match making mentoring program for women from college through retirement. Connect with Vicki and join the experience.

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