Developing Managerial Courage In Retail Leaders

Developing Managerial Courage In Retail Leaders

As I mentioned in my last post, it has been a wildly busy several weeks. I am currently working on an amazing project with a company that is extremely challenged with their Store Leader level of employee. The company I am currently supporting does not invest in their people. Store leaders are selected using an outdated set of criteria – with the most important and valued “skill” that their store leaders can possess is [wait for it…] compliance.

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Very rarely am I working with an organization that is extremely healthy – sometimes it happens [but not very often] – in the case of this project, the company is struggling. It is struggling with its organizational culture, employee retention, employee development, customer experience, selling culture, and a future vision [as they are consistently talking about “yesterday” instead of tomorrow]. The store teams are very used to being spoon-fed direction and micro-managed via email and checklists – especially over the past year or so. They are conditioned to escalating even the smallest matters to the next level of leadership to avoid responsibility for any decision. I thrive on challenges and this project is certainly motivating me to find ways to inspire and challenge people who are, frankly, very cautious, extremely skilled at upward delegation, and adept at playing the victim of their environment.

Managerial courage has been a huge developmental initiative in the few weeks I have been with this group. Holding store and field leadership accountable for making decisions and pushing through the discomfort to find out how they can embrace their role as a leader and become highly-effective in their role and how learning and refining this skill will benefit them in the future. Here are some of those things we have been discussing ad nauseum:

Tips For Developing Managerial Courage In Retail Leaders

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  • Make sure you possess all relevant and important information on the topic you need to address. Nothing kills leadership credibility faster than inaccurate information.
  • Share the information only with the person/people involved – do not get anyone else involved in the issue
  • Especially if you have a difficult message to deliver – make sure you stay on topic and get to the point without much emotion or editorializing. People are pretty smart, and usually if it is an unpleasant topic they are aware there is an issue – so say what you need to say directly and respectfully. Have a solution to the issue(s) prepared going into the conversation. A true sign of leadership is being able to support your team to overcome their obstacles and drive a solution-focused culture for your team while holding them accountable for their performance.
  • Guide your leaders to be absolutely prepared for a variety of feelings they may witness when addressing issues on their team.  If you are unsure of what response you will encounter – partner with your supervisor or HR for support. Being calm and organized in all situations will set the tone that others are open to listening and providing feedback for.

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  • Timing and attitude is everything – When you or the other party/parties are frustrated or upset your message will not be absorbed in the way you hope it to be and the issue(s) could be exacerbated by addressing it at the wrong time and with the wrong approach.
  • Be objective – if you are infusing your personal beliefs/feelings, you are not being objective. Are your intentions benevolent and in the best interest of productivity and fairness or do you have an interest in seeing one side “win” over the other? In order to be a strong leader you need to maintain an elevated level of objectivity and not allow personal opinion to blur your approach to the situation.
  • Keep an open mind – through empathy and involvement – practice the art of listening and understanding others perspectives will help bring clarity and transparency to a situation. When you are open to others ideas and thoughts and you invest in truly listening to understand, you can support an open, honest, and respectful dialog when discussing issues with your team or colleagues.

As the retail workplace continues to evolve, possessing the ability to have critical conversations is an absolute must. One of the reasons that the teams are in such a challenging and ineffective state is because these dialogs do not occur. There are months [and in some cases years – hard to believe, I know] of harbored resentment and buried issues that are impeding the progress of the teams and the business which is absolutely contributing to the struggles of the organization. Addressing this crucial competency with store and field leaders who are not accustomed to dealing with the yucky stuff in their business is not an easy task. You can’t just have a conversation with someone and…voilà – they now have managerial courage. Like all of the necessary and valuable leadership competencies – we must take the time to guide and develop our team to be proficient and confident in this skill.

How To Leverage Managerial Courage Development

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  • Practice strategic thinking; the ability to think two or three weeks [and in the future – months] ahead is critical to retail leadership success.  Having the ability to assess how both the negative and positive take-aways your team member can make to the vision and direction of where the organization, store, and team are moving.
    • When difficult conversations must take place, great leaders have the ability to link the conversation to the bigger picture through initial short term activities which can begin support the health of the business and the collective team.
  • To keep conversations on pace and to the point it is crucial to practice your message before delivering to others. However, in order to gain perspective to ensure you are viewing the issue considering all points-of-view, company & customer impact, and future implications. By being response ready and confident during tough dialogs you can put concerns at ease and garner buy-in from those who usually enjoy challenging you.
  • Ask questions to continue to gather the most accurate information regarding the situation, but also to catalyze creativity and innovation. Sometimes people need to see things from a different perspective – asking thought-provoking questions and by requiring ideas and solutions during dialogs pushes complacent or apathetic “managers” to get beyond the pedestrian “I have a problem and I need you to fix it” mindset. Create constructive challenge can help people – who bring issues to their supervisor – start to think of ways to overcome the challenges.

Learning to take an intelligent risk requires a methodical and thoughtful approach to the issue(s). The nucleus of this method is making success more likely while avoiding unproductive, inefficient, or irrational behavior.

Does the situation call for immediate, swift action or something more nuanced and benign? Courage is not about wasting leadership or political savvy on low-priority issues or those that make you feel powerful. It is about doing what is right and necessary – acting in the best interests of your organization and your team. When dealing with very ineffective and under-skilled store and field leaders – you will find that everything is a disaster. Everyone’s issues are the most important and dire – regardless of how truly unimportant and insignificant to the business they are.

Steps To Addressing Issues Using Managerial Courage

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  • Set A Goal For The Desired Outcome: What does success look like in this situation? Is it achievable and will it satisfy most of the parties involved? If my primary goal is organizational, does it support or advance my organizations vision and values? If my primary goal is personal, does it derive solely from my personal ambitions or also from a desire for my organization’s greater good? Is it selfless or selfish?
  • Determining and Assigning The Goal’s Importance In The Business: Identify just how important is it that you achieve your goal or goals? If you don’t do something about the current state of affairs, will your company, customer, or team suffer? Will your professional brand suffer? What are the potential issues should you put this issue on the back burner in lieu of something that you deem more critical and important to the business? In order to prioritize and manage issues – you need to identify which are business critical. This is where leadership can support this competency. Not by solving the issue(s) – but through guidance.
  • Tipping The Power Balance: Employees often assume that power in retail is a simple matter of position on the organizational chart. In attempting to please those their supervisors, many people choose never to take a stand. But in reality, even those in senior- and executive- level leadership give power to anyone on whom they are dependent, whether for respect, advice, appreciation, or partnership. “Power” is something over which we really do have considerable control. By establishing relationships that are built around respect, transparency, and openness with those around you. For example, you gain credibility over people who otherwise ignore and challenge you just because they don’t respect you. Building a credible, transparent, authentic , and genuine leadership style gives you a broader base from which to make bold moves and invite others along for the journey.
  • Risk & Benefit Assessment: Who stands to win? Who stands to lose? What are the potential ramifications of those results? What are the chances that your reputation will be tarnished if you move forward? Will you lose respect the respect of your team and your leadership? When addressing challenges in the business there is always someone who will be unhappy with the outcome but through open dialog and explaining the whys you will help people understand the benefits of the outcome. In retail leadership we are so scared to address the issue and happy to use hope as a strategy that the “thing” will resolved itself or disappear. Using hope as the primary strategy you will absolutely see the issue increase in mass and spread to other areas of the business. Addressing issues before they become a “thing” will support a culture that is focused on solutions and doing the right thing – even when no one is looking.
  • Timing Is Everything: Why am I addressing this now? Am I contemplating deliberate action or an impulsive one? How long would it take to become better prepared? What are the pros and cons of waiting a day, two days, a week? Can I take steps now that will create a foundation for a courageous move later? Am I both emotionally & mentally prepared to address this issue? Do I have all of the facts needed to support the right decision? Do I have the expertise, communication skills, track record, and credibility to make this work?
  • Have A Plan B: Especially if you are new to this “courage” competency – contingency planning is really about resourcefulness – which we retail folks are pretty darn good at. Retail leaders who take bold risks and succeed are versatile thinkers; they ready themselves with alternative ideas that can influence positive resolution.

The term “managerial courage” for me, reflects this need for leaders to become leaders of credibility It is through personal action and workplace relationships that leaders develop trust and gain commitment from employees. When this is made a priority – you will find that your team is inclined to proactively surface issues that negatively effect their morale. You will feel a level of comfort addressing issues when they arise – not waiting for them to become business impediments. It is a skill that all great teams and a leaders embrace, value, and exercise consistently.


Founder and Editor in Chief of Excellence In Retail. Published writer. Frequent Podcast Guest. Speaker. Twenty year [oy vey!] retailer. I am passionate about leadership development and workplace culture. 646 246 1380 | [No Sales Contact, please} But it you want to call just to say hello or have a question - that's awesome!

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