Montgomery and His Chief of Staff (#256)

This year, I am doing a series on leaders and leadership in the European Theater of Operations (ETO) in World War II. This is 8th in the series. Check out the blog to see them all or go to the links at the bottom of this article to see the most recent ones.

In America, historians bash Field Marshal Bernard Montgomery, the highest ranking British general in Europe. On the other hand, in the United Kingdom, British historians love him. Whichever camp you are in, “Monty” was a polarizing figure. I wrote previously on Montgomery’s Leadership Lessons so I thought it would be interesting to see how he ran his staff — through his remarkable Chief of Staff, General Freddie de Guingand.

Montgomery’s Chief of Staff — General Freddie de Guingand

For those that didn’t read the previous article, Field Marshal Bernard Law Montgomery, 1st Viscount Montgomery of Alamein, was also known as “Monty.” He was the most well-known British general of World War II. He commanded all ground forces at D-Day and was instrumental in expanding the D-Day landing plan from 3 beaches to 5 beaches. In addition, Field Marshal Montgomery was unwavering in the face of adversity and was notorious for his sharp wit, self-promotion, and direct attitude. Also, he was highly appreciated among his subordinates as an exceptional commanding officer. Nevertheless, the higher ranks often found Monty difficult to work with including Eisenhower. Even Churchill, who later became one of his most faithful friends once said of him: “in defeat, unbeatable: in victory, unbearable.”

From North Africa, to Sicily, to Northeastern Europe, Montgomery relied on General Freddie de Guingand as his Chief of Staff. This was highly unusual in the British Army — every other British Army organization had a chief of the operations staff and a chief of the administrative staff. In the typical British structure it was up to the commanding general to synchronize the two parts of the staff. Montgomery had been in a unit in World War I that had used a chief of staff. The American Army also used a Chief of Staff.

Bucking conventional wisdom, Montgomery appointed de Guingand to synchronize the entire staff and serve as his chief of staff when he took over Eighth Army in North Africa in 1942. He later described Freddie by saying: “His fertile brain was full of ideas and he was never defeated by the difficulties of any problem. He could take from me an outline conception of a plan, work out the staff details, and let me know quickly of it was possible from a staff point of view: and if not, what changes in substance were desirable. He accepted responsibility readily. I gave him full powers. If he couldn't get hold of me he would give a major decision himself and I never once questioned any such decision. I trusted him completely; he seemed to know instinctively what I would do in any given situation, and he was always right.”

The two worked together in the North African, Sicilian, Italian, and Northern European campaigns.

General Francius Wilfred de Guingand

Major General Francis Wilfred de Guingand, known as Freddie, was a highly respected British military officer who served as the Chief of Staff to Field Marshal Bernard Montgomery during World War II. De Guingand had a distinguished military career prior to his appointment as Montgomery's Chief of Staff. Commissioned after the end of World War I, he served in India, Egypt, Africa, and Palestine before World War II broke out. Freddie was not the epitome of good health — throughout his adult life, Freddie dealt with debilitating gallstones.

As Montgomery's Chief of Staff, de Guingand played a central role in planning and executing the Normandy landings. In the lead up to Operation Overlord, Montgomery toured the countryside talking to the troops while de Guingand and the staff worked out the logistics and operational details of the plan. In Field Marshal Montgomery’s absence, de Guingand was in charge of the headquarters at St Paul's. He chaired the daily staff conferences and attended inter-staff meetings with his opposite numbers from the Royal Navy and Royal Air Force. De Guingand's organizational skills and ability to manage complex operations proved to be essential to the success of the North African, Sicilian, Italian, and European campaigns. In addition to his military expertise, de Guingand was also known for his diplomatic skills. He was highly respected by his American counterparts and was able to build a strong relationship with Bedell Smith to ensure effective collaboration and coordination among the Allies.

Interestingly, Montgomery opted to not move the large headquarters from England to Bayeux, France until the end of July — almost 45 days later. De Guingand and Montgomery talked daily but the two worked remotely before remote worked was en vogue.

General Omar Bradley later described de Gunigand by saying “Like Bedell Smith, a brilliant staff officer dedicated to anonymity and his job, he went one step further by complementing the personality of his chief. In Freddy, as de Guingand was affectionately known to the American command, we found a ready intermediary and peacemaker. For whenever the distant attitude of Montgomery ruffled a US staff, it was good old cheerful Freddy who came down to smooth things over. An able and professional soldier, de Guingand had served Montgomery since El Alamein. He was an able and sympathetic administrator, wise to and unpanicked by the crises and problems of war. Although Freddy's popularity with the American command stemmed partly from the adeptness with which he bridged our good relations, he was uncompromisingly devoted and loyal to his chief. De Guingand earned our affection not because he toadied to us but because he helped to compose our differences with justice and discretion.”

Application

Retired General Stanley McChrystal has written and spoken extensively about the role of the Chief of Staff in a military or civilian organization. Today, the Chief of Staff should be a trusted and effective advisor to the leader, helps to manage the day-to-day operations of the organization, helps to balance competing demands and interests within the organization, and assists in building relationships and communicating effectively with a wide range of stakeholders. Ultimately, the Chief of Staff is a critical member of any high-performing team and is someone who can help the leader achieve their goals and objectives. General General Freddie de Guingand epitomized this definition for Montgomery.

The management of the day-to-day operations in a company are challenging. Most companies I have worked with don’t have a dedicated chief of staff. Or one that helps the Chief Executive Officer oversome her shortcomings. Or if the company does have a chief of staff, they are not empowered to act in the same way General de Guingand did for Montgomery during World War II. One company, in particular, had an amazing CEO that was fantastic with the board, with investors, and with the media. She struggled, though, to manage her 15 direct reports and the day-to-day operation of the company. If she had hired and empowered a chief of staff, the business would have been a lot better off.

Does your organization have a chief of staff? Are they empowered to plan, manage the day-to-day operation, and make decisions? Could your organization benefit from having a true chief of staff?

Conclusion

The last five blog posts on leaders and leadership from the World War II European Theater of Operations are:

Liberty Ships, LVCPs, Shermans, and Mustangs

Walter Bedell Smith

Ike’s Flaws

Ike’s 8 Characteristics of Leadership

Interested in bringing your team to Leadership Experience that uses historic case studies at battlefields and museums, like Freddie de Guingand as a Chief of Staff during D-Day to enhance your team’s leadership today? TFCG offers the D-Day, Market-Garden, and Battle of the Bulge Leadership Experiences in Europe. TFCG also offers the Eisenhower, Currahee!, the War in the Pacific Museum, and Pearl Harbor Leadership Experiences in the United States. Send me an email and we can start the discussion today about building better leaders in your organization using a historic Leadership Experience. Or click on one of the pictures to learn more.

In the meantime, go on the offensive and ensure your organization has a Chief of Staff as effective as General Freddie de Guingand.

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General James Gavin (#257)

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Invasion of Ukraine, March 2023 SITREP (#255)